How much Multiclassing can you pack into a viable character?

[hex37]

Question in the title. Some friends of mine were thinking about running a one-shot in a battle arena with all level 20 characters, and for ****s and giggles, I wanted to use that as an opportunity to multiclass the **** out of a character.

Any ideas for a build? I'm pretty good with macros, so I'm pretty good with stacking on like 20 damage modifiers to a roll. Naturally, we should be avoiding any multiclass levels beyond 4, so extra attack options might be excluded? I'm still trying to cobble things together.

[Galithar]

Question in the title. Some friends of mine were thinking about running a one-shot in a battle arena with all level 20 characters, and for ****s and giggles, I wanted to use that as an opportunity to multiclass the **** out of a character.

Any ideas for a build? I'm pretty good with macros, so I'm pretty good with stacking on like 20 damage modifiers to a roll. Naturally, we should be avoiding any levels beyond level 4, so extra attack options might be excluded from the build.

Paladin 6/Barbarian 3/Fighter 2/Warlock 3/Rogue 3/Sorcerer 3

Paladin: Extra Attack, Smites and Aura.
Barbarian: Bear Totem Rage resistance
Fighter: Fighting Style and Action Surge
Warlock/Hexblade: Smite fuel, devil's sight, Ranged attack option in EB/Agonizing Blast, Cha attack/damage rolls, Hexblade curse
Rogue/Swashbuckler: Sneak attack and expertise in case of grapple checks
Sorcerer: Quicken for a bonus action EB and smite fuel

Turn 1
Bonus Action Hexblade Curse on biggest threat
Action: EB said threat
Move: Get to cover if possible to about others round one Nova

Turn 2
Bonus Action: Rage
Action: Attack
Action Surge: Attack

Turn 3: basically keep hitting things with your chosen pointy object. Smite when appropriate.

Damage per attack action:
(4d6+4) (It'll be hard to have Cha thought then 18 with this whacky but because only 1 AS I)

That is the most classes I could pack into one character and still have some ability to fight. Obviously you can drop certain classes and add levels elsewhere to get ASIs and make it a lot stronger though.

Edit: Almost forgot pact of the Chain for Warlock to get an imp Invisible help action.
And again, not by any means super efficient. I just tried to quickly pack on as many classes as possible and have each actually contribute something.

[Man_Over_Game]

Question in the title. Some friends of mine were thinking about running a one-shot in a battle arena with all level 20 characters, and for ****s and giggles, I wanted to use that as an opportunity to multiclass the **** out of a character.

Any ideas for a build? I'm pretty good with macros, so I'm pretty good with stacking on like 20 damage modifiers to a roll. Naturally, we should be avoiding any multiclass levels beyond 4, so extra attack options might be excluded? I'm still trying to cobble things together.

Few rules of thumb for a character:

Don't multiclass to-from mages, unless it's for a specific benefit (like armor, fueling spell slots for one side or the other, or the Shield spell)
Don't multiclass more than 5 levels into more than one class that gets Extra Attack, to avoid a redundant level
Don't multiclasses classes that have conflicting primary modifiers.
Avoid having redundant features (like Monk Step of the Wind vs. Rogue Cunning Action)

Other than that, go nuts.

You want an Archer? 4 Ranger, 5 Fighter, 11 Rogue. Or any variant of these.

You want a tank? Barbarian 8, Fighter 4, Rogue 4, Paladin 4.

You want a skirmisher? Monk 5, Fighter 4, Barbarian 4, Rogue 4, Ranger 3.


When multiclassing casters, you really need to focus on the "Master" and "Slave" concept, where one does all the heavy lifting, and the others fuel low level spells and features.

A few examples:

Sorcerer 17, Warlock 1, Paladin 1, Bard 1.
Druid 17, Ranger 1, Monk 2.

[JoeJ]

If this is just a one-shot, you might want to consider the character of all classes.

[Griswold]

You can do pretty well with 8 classes:

Hunter Ranger 6/Paladin 2/Barbarian 2/Battlemaster Fighter 3/Rogue 1/Cleric 1/Sorcerer 3/Abjurer Wizard 2

Ranger: Extra attack + third attack with Hunter + 2nd level ranger spells
Paladin: Smites
Barbarian: Rage + Reckless Attack
Fighter: Action Surge. Battlemaster for more combat utility, or champion to get tons of chances to crit with reckless attack.
Rogue: Expertise, extra skill, sneak attack. This plus Pass Without Trace = amazing at stealth.
Cleric: Life for best out-of-combat healing with upcast goodberries and healing spirit. Order and Knowledge are fun dips too.
Sorcerer: Metamagic for bonus action spell shenanigans.
Abjurer Wizard: Extra hp for tanking even while raging, gets you access to awesome rituals.

You've got three different fighting styles. Protection + the one you actually want (THF or duelling), so your AC is amazing. You can reckless attack all day if you like.

[hex37]

I ended up mixing a total of 6 classes together, with the idea that I'm going to make a character that really only does damage once. Just once. It's honestly going to be harder to code the macro in Roll20 than it will be to play, but... I like challenges?

1-Pump Chump
Race: Half-Elf
Weapon: Greatsword

Brute Fighter 6
-1d4 passive damage buff
-Fighting style: Great Weapon Fighting
-Feat: Great Weapon Master
-Feat: Elven Accuracy (Triple advantage, Gets Cha to 18 with point-buy)

Assassin Rogue 3
-Expertise on Stealth
-Sneak attack
-Crit and automatic advantage during surprise round

Gloom Stalker Ranger 3
-Fighting Style: Mariner for parkour and a little extra AC
-Dread Ambusher gives an extra attack per attack action first turn
-Hunter's mark

Spore Druid 3
-Pass without Trace
-Symbiotic Entity +1d6 Poison damage to melee

Hexblade Warlock 3
-Hexblade's Curse for flat +6 to damage
-Used with Pact of the Blade / Improved Pact Weapon, Makes the Greatsword use a CHA modifier for attack/damage, causing Elven Accuracy to affect it.

Paladin 2
-Fighting style: Defense for an extra +1 AC
-Divine Smite: allowing you to blow all of your remaining spell slots during round 1. How many do we get again?

Multiclass spellcaster Levels:
1(Paladin) + 3(Druid) + Ranger(1) which gives us-
4 1st level slots,
3 2nd level slots,
2 3rd level slots.

Naturally, Warlock spells don't count, but that is OK. We can use them for other things that help us get in close for Assassination.

Setup:
- Use Stealth expertise, Pass without Trace, and whatever else you packed into your Warlock-toolkit to get into melee unnoticed.
- Use Hunter's mark, Hexblade's Curse and Symbiotic Entity on target.
- Make 7 attacks (Triple advantage, all hits are critical so Great-Weapon Master procs if you hit even 1 of the previous 6.)

Spoiler: Damage breakdown

Show

Attack 1 damage:
4d6(Weapon crit)
+ 4d4(Brute Force crit)
+ 4d6(Sneak attack crit)
+ 2d6(Symbiotic Entity crit)
+ 2d6(Hunter's Mark crit)
+ 6d8(3rd level smite crit)
+ 4(Charisma modifier)
+ 6(Hexblade's Curse)
+ 6(Proficiency)
+ 10(GWM) = 94 damage on average
Attack 2 damage:
4d6(Weapon crit)
+ 4d4(Brute Force crit)
+ 2d6(Symbiotic Entity crit)
+ 2d6(Hunter's Mark crit)
+ 6d8(3rd level smite crit)
+ 4(Charisma modifier)
+ 6(Hexblade's Curse)
+ 6(Proficiency)
+ 10(GWM) = 82 damage on average
Attack 3 damage:
4d6(Weapon crit)
+ 4d4(Brute Force crit)
+ 2d6(Symbiotic Entity crit)
+ 2d6(Hunter's Mark crit)
+ 2d8(Gloomstalker round 1 crit (Also is what allows this attack))
+ 4d8(2nd level smite crit)
+ 4(Charisma modifier)
+ 6(Hexblade's Curse)
+ 6(Proficiency)
+ 10(GWM) = 82 damage on average
Attack 4 damage:
4d6(Weapon crit)
+ 4d4(Brute Force crit)
+ 2d6(Symbiotic Entity crit)
+ 2d6(Hunter's Mark crit)
+ 4d8(2nd level smite crit)
+ 4(Charisma modifier)
+ 6(Hexblade's Curse)
+ 6(Proficiency)
+ 10(GWM) = 74 damage on average
Attack 5 damage:
4d6(Weapon crit)
+ 4d4(Brute Force crit)
+ 2d6(Symbiotic Entity crit)
+ 2d6(Hunter's Mark crit)
+ 2d8(1st level smite crit (Ran out of 2nd level slots b/c of pass without trace))
+ 4(Charisma modifier)
+ 6(Hexblade's Curse)
+ 6(Proficiency)
+ 10(GWM) = 66 damage on average
Attack 6 damage:
4d6(Weapon crit)
+ 4d4(Brute Force crit)
+ 2d6(Symbiotic Entity crit)
+ 2d6(Hunter's Mark crit)
+ 2d8(1st level smite crit)
+ 2d8(Gloomstalker round 1 crit (Also is what allows this attack))
+ 4(Charisma modifier)
+ 6(Hexblade's Curse)
+ 6(Proficiency)
+ 10(GWM) = 74 damage on average
Attack 7 damage:
4d6(Weapon crit)
+ 4d4(Brute Force crit)
+ 2d6(Symbiotic Entity crit)
+ 2d6(Hunter's Mark crit)
+ 2d8(1st level smite crit)
+ 4(Charisma modifier)
+ 6(Hexblade's Curse)
+ 6(Proficiency)
+ 10(GWM) = 66 damage on average

Total average damage for the Assassination: 538. 468, if you want to make absolutely sure that everything hits.

Weaknesses:
- Bliiiindsiiight
- The GM having half-an idea what an Assassin Rogue -anything- does, and planning accordingly
- Round 2
- Having to fight more than once

[Throne12]

Get 13 in all stats but charisma. Get charisma as high as possible. Then take 2 levels of warlock this is for EB + Agonizing blast there your done. Now take a level in every class and see what you can do.

[Aquillion]

Rogue (Assassin) 3, for Assassinate
Ranger (Gloom Stalker) 5, for Hunter's Mark, Dread Ambusher, Umbral Sight, Wisdom to initiative, Extra Attack, and an ASI.
Fighter (Battle Master) 3 for Action Surge and maneuvers.
Warlock (Hexblade) 1 to attack with Charisma
Paladin 2, for Divine Smite
Swords Bard 4 for Blade Flourish, Jack of All Trades to initiative, higher-level spell slots for your Divine Smite, and an ASI.
Druid 2 (Circle of Spores), for Symbiotic Entity.

This is fairly MAD (you benefit from Wisdom, Charisma, Dexterity, and Constitution, and need 13 in a bunch of stats just for all the multiclassing), and you only get two ASIs, so you'd better roll your stats and roll well. Rolling an 18 for Charisma and choosing a race that boosts it is almost essential. But with Wisdom + Dexterity + Jack of All Trades to initiative, you're usually going to go first anyway.

Your initial auto-critical will be obscene, hitting three times and doubling your smite, your spores on each hit, your flourish, your sneak attack, your Battle Master maneuver dice, your hunter's mark damage on each hit, your Dread Ambusher extra damage and more... and then you use your Action Surge and do it all again.

Your spellcasting level is 9, giving you 5th-level slots (but obviously not spells, so choose things that upcast well); while your spells are limited, your high Charisma makes you good at using them, so you should have plenty of valuable buffs or utility. More importantly, you can use those slots to Smite for 5d8 on every single attack in your initial auto-critical ambush.

You also have expertise four times, a ton of skills, and Jack of All Trades, so you're going to be valuable outside of combat.

You could probably make this a bit better by removing a few classes and rearranging things to get more ASIs, among other things (druid and bard are gratuitous), but they're important to get enough spell slots to do a 5d8 smite on every single attack in your initial nova, and they all add at least a little damage to your initial attack, plus plenty of utility.

Note that you pretty much need a short rest after every serious fight if you want to operate at full power. Still, your wide range of skills, cantrips, low-level utility magic and so on means that you'll usually have something to at least contribute, and when you go all-out you can drop or severely injure almost anything in the first round.

If you're worried about going for long periods without rest, consider trading one of those levels for another level in Warlock to take Agonizing Blast, giving you reliable ranged attacks for the entire game whenever you're not doing your one-hit kill trick.

EDIT: Haha, someone basically posted this build above, oops. Theirs looks better, but involves fewer classes! I think squeezing Swords Bard in there is a weaker choice, but doable - though its value depends heavily on if your DM allows you to get your Blade Flourish only once a turn, once an attack action (provided you always pick the same option), or once an attack (provided you always pick the same option.) More importantly, though, it also adds another 4d8 (ish) to all your attacks by pushing your smites up to the maximum and giving you enough spell slots to boost almost all your attacks that far, plus it gives you a bit more out-of-combat utility.

The reaaally big problem with my version is that GWM + Elven Accuracy consumes literally all your ASIs, so you'd better roll one 18 and everything else above 13.

- Round 2
- Having to fight more than once

Since you went to Warlock 3, you can get EB + Agonizing Blast. You definitely won't be a top-tier damage dealer outside of your initial nova, but you'll deal reasonably consistent ranged damage for whenever your main trick doesn't work.

Although really, as long as you can get advantage you're not terrible in melee after your initial attack, either. You continue to add spores, brute, and hunter's mark to all your attacks; you roll three times and crit on a 18-20 due to Hexblade, getting another GWM attack when you do, and with three rolls you can GWM everything as long as you have advantage.

4d4(Brute Force crit)

Shouldn't that be 2d4? Or am I missing something?

EDIT: Ooof, my version also suffers from unable to use GWM due to not being able to apply the Hexblade benefit to a non-heavy weapon. Mike Mearls has said that a 1d8 one-handed heavy weapon is notionally balanced (with specific reference to it working with GWM), but I'm not sure any DMs would allow that given how strong GWM is already. I don't think there's a way to squeeze in Bard and still have it work, unfortunately.

But for your version, I would recommend dumping three levels of Fighter, and getting your ASIs and extra attack by pushing Druid to 4 and Ranger to 5, since that gets you everything important you were getting from those fighter levels, plus more spell levels (and therefore better smites), plus better spells known and improved wild shape (which you will probably never use, but for this build it's probably better than the slightly bigger HD you get from getting those things out of Fighter instead.)

At that point you cast as a 7th level caster, giving you the 4th level slots to do 5d8 smites on your first one and 4d8 to 3d8 on most other attacks, effectively adding 2d8 to each attack in your end result.

Ranger 5 also already gives you Pass Without Trace, which was the main reason you went past Druid 2... but we need that ASI, and I think it's better to get it through two Druid levels than one Fighter level in order to get better smites. Actually, since your half-caster levels are odd, you could also go Druid 2, Ranger 5, Fighter 4, and Paladin 3, and at least be a 6th level caster. Or put that 3rd Paladin level in Warlock if you want another ASI.

Assuming the 4d4 Brute bonus was an error (it's 2d4, right?), the Battle Master is slightly better for your nova round - blowing all your superiority dice is 4d8 vs. 7d4, plus you get the maneuver benefits... not that those are a big deal given that your target is almost definitely dead. Of course, going that route makes you suck even more after your initial nova.

[Alucard89]

For such one shot I would ignore Aura on Paladin and go:

Paladin 2, 3 Champion, 5 Barbarian (Berserker), 10 Whisper Bard.

Reckless Attacks gives advantage on demand (no action required), Champion 19-20 crit range, 11 level caster gives 4/3/3/3/2/1 spell slots for smitting. You also have Rage resistance to charm and fear, bonus attack in Frenzy, Action Surge, Extra attack and Bard gives you 5d6 extra dmg per one turn + Magic Secrets (2 spells- take Armor of Agathys)

Pre-Cast: Armor of Agathys from 6th level slot: +30 HP and 30 retaliation damage to enemies. No concentration required. Will combo well with Rage resistances.

First turn:

Bonus Action- Frenzy
Action: Reckless Attacks: 2 attacks with max smites attached + Action Surge: 2 attacks with max smites attached. Attach 5d6 Physic Blades to one strike, best to the one you crit with.

Second turn: Frenzy bonus attack + 2 attacks.

ASI: you will have only 3 ASI. I would take GWM and 2x +2 STR for 20 STR and just go to town with it.

[Misterwhisper]

Draconic sorcerer fire 6, celestial warlock 6, arcana cleric 8.
Tiefling with elemental affinity and flames of phelgathos feats.

Captain fire guy.

Knowledge cleric 2/lore bard 3/scout rouge 11/warlock chain 4.
play as a half elf
skilled, prodigy and elven accuracy.

Skill monkey.

[sithlordnergal]

Here's a rather fun build I know, and have kind of played before:

Race: Half Elf

Spoiler: Ability Scores

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Assuming a 27 point buy, start with:

Str: 15

Dex: 8

Con: 12

Int: 8

Wis: 16

Cha: 16

Spoiler: Classes

Show

Paladin of Vengeance: 6

Druid of Dreams: 4

Bard College of Swords: 4

Divine Soul Sorcerer: 4

Fighter: 2

Spoiler: ASI's

Show

You get a grand total of 4 ASIs, you want to get Polearm Master, Warcaster, Wisdom to 20

Make sure you get the Shield spell and Shillelgah, and grab yourself a quartertaff. You should aim to either wear plate armor, which is technically allowed, or get some non-metal plate armor if your DM doesn't like the idea of druids wearing metal. You can then cast Shillelgah for a d8 wisdom based attack and use it for the polearm master bonus action attack. You can smitre on all of those attacks, and add a d6 points of damage with Blade Flourish. then do it all again with action surge. You'll also have healing from Druid, Bardic Inspiration, Paladin aura and healing, and other stuff.

[bid]

-Used with Pact of the Blade / Improved Pact Weapon, Makes the Greatsword use a CHA modifier for attack/damage, causing Elven Accuracy to affect it.

No sneak attack, not a finesse weapon. There's a 2d4 heavy finesse though.

[Aquillion]

Make sure you get the Shield spell and Shillelgah, and grab yourself a quartertaff. You should aim to either wear plate armor, which is technically allowed, or get some non-metal plate armor if your DM doesn't like the idea of druids wearing metal. You can then cast Shillelgah for a d8 wisdom based attack and use it for the polearm master bonus action attack. You can smitre on all of those attacks, and add a d6 points of damage with Blade Flourish. then do it all again with action surge. You'll also have healing from Druid, Bardic Inspiration, Paladin aura and healing, and other stuff.

I mentioned this above, but RAI is that you can only Blade Flourish once a turn. Personally I think that regardless of intent, the RAW clearly allows you to use it multiple times if you choose the same option each time, and that as long as you don't allow the AC-boosting one to stack it's fine.

Then again, Blades is only a weaker option by Bard standards. (You have no idea how weird it feels to type that sentence after so many editions of Bards sucking.) Going with that interpretation means that Blade bards with the right spell selections (eg. Swift Quiver and an archer build) can be among the best DPR builds in the game on top of still being a powerful full caster with a strong spell list.

No sneak attack, not a finesse weapon. There's a 2d4 heavy finesse though.

Really? Where? What is it? That changes the build I outlined above a bit, since it eliminates the need for Warlock levels to enable Elven Accuracy + GWM.

[Meichrob7]

This isn’t max multiclass but a fun little 3 class combo is
Battlemaster 11
Gloom stalker 4/5
Assassin 4/5
Hexblade 0/1

Gloom stalker and assassin can swap that 5th level or you can give it to hexblade for maximum damage, but I wanted pass w/o more than evasion or the curse.

Battlemaster gives you 3 attacks and lets you spend pretty much all of those superiority dice in your first turn, meaning that if you just spam one effect the enemy will probably fail the save at least once so you can pretty reliably disarm people. There’s also the eternally valuable action surge.

Gloom stalker gives you greater invisibility permenantly as long as you’re in the dark, which imo happens most of the time in dnd. Gloom also gives you another attack on your attack action your first round of combat. Combined with action surge you’re getting 8 attacks off on turn one.

Assassin is picked for obvious reasons that need not be explained.

If your dm is more lenient about stealth and getting surprise then losing Pass w/o for hexblade’s curse Is very much worth it as it adds twice as much damage as hunters Mark would and doesn’t need concentration. However at some point you’ve reached enough damage to kill whatever is in front of you as long as you have surprise, so triggering that surprise becomes more important than adding to the damage you’d do.

Feats are elven accuracy and alert for max nova. If you wanted more reliable damage each round instead of dumping every resource at once then sharpshooter works great with battlemaster because if you use the superiority dice to add accuracy and then trade accuracy for +10 damage, you end up with a lot more damage and on average a higher bonus to hit than if you’d just done a normal attack with one of the maneuvers that add damage. The only reason it’s not super useful here is because it’s not dice damage and assassin cries don’t double flat bonuses to damage.

This build was designed around having the oathbow and blowing someone up immediately. We were running a level 20 PvP battle royal and my character was pretty lazy so he just made a deal with the Druid to instakill the party wizard and then give up for 1/2 of the final rewards. If you go super ham into nova you can only really kill one person at most so I figured I’d make a deal with the second biggest threat to take out the single biggest threat.

[MThurston]

One little hiccup.

When you sneak attack you have to roll initiative. So if your target beats your roll, you do not auto crit.

[Particle_Man]

In another thread people are talking about love of cantrips. So if one went "all out" how many cantrips could one get through multi-classing? And is there a way to make that a viable character too?

Edit: I posted too soon. Sadly, the grammar of the warning was off, saying "please post again in 1 seconds".

[Aquillion]

One little hiccup.

When you sneak attack you have to roll initiative. So if your target beats your roll, you do not auto crit.

Gloom Stalker gives Wisdom to Initiative, so provided you have both high Dex and high Wisdom, you're likely to win initiative more often than not.

Also, if you get a surprise round then you get to assassinate anyone you want in it regardless of initiative. And this build is pretty good at getting that, with Expertise in Stealth from Rogue and Pass Without Trace from Ranger 5.

Although both me and someone else posted builds of this nature above that use more multiclassing. See the builds above - if you're willing to switch to close range, you can add two levels of Paladin for smite damage (which the crit multiplies), and probably also Spore Druid 2 for both the spore damage and more spell slots to fuel your smites. GWM also combines extremely well with ambushes (not because of the bonus damage, although that's nice, but because the guaranteed crits means it's another attack.)

[bid]

Also, if you get a surprise round then you get to assassinate anyone you want in it regardless of initiative. And this build is pretty good at getting that, with Expertise in Stealth from Rogue and Pass Without Trace from Ranger 5.

There's no surprise round in 5e. You can still fail to act first once in a while.

[Aquillion]

There's no surprise round in 5e. You can still fail to act first once in a while.

Huh?

Surprise

A band of adventurers sneaks up on a Bandit camp, springing from the trees to Attack them. A Gelatinous Cube glides down a dungeon passage, unnoticed by the adventurers until the cube engulfs one of them. In these situations, one side of the battle gains Surprise over the other.

The GM determines who might be surprised. If neither side tries to be stealthy, they automatically notice each other. Otherwise, the GM compares the Dexterity (Stealth) checks of anyone Hiding with the passive Wisdom (Perception) score of each creature on the opposing side. Any character or monster that doesn’t notice a threat is surprised at the start of the encounter.

If you’re surprised, you can’t move or take an action on your first turn of the combat, and you can’t take a Reaction until that turn ends. A member of a group can be surprised even if the other members aren’t.

Surprise is a thing in 5e, even if it's not formally called a "surprise round."

[Galithar]

Huh?
Surprise is a thing in 5e, even if it's not formally called a "surprise round."

They are taking about characters/enemies with things like 'alert' that prevent them from being surprised I believe.

I don't like that it is technically possible for a character that is ambushed and doesn't see the enemy yet to act before then, but technically it is RAW. I suggest anyone else that dislikes that rule to houserule that being the surprising force gives an automatic Nat 20 initiative roll (first round only. Follow their natural initiative roll starting in round 2) It still allows for someone with massive bonuses to act before their ambusher, but other then builds that are super focused on this it should rarely if ever allow an ambushed character to act before the ambusher.

The first time I clashed with this RAW the party walked near a tower that had archers hiding up top to ambush them. Someone with alert rolled higher initiative and I foolishly allowed them to attack (and kill) an ambusher that they shouldn't have been aware of yet. I discussed with my players and made modifications after that incident with table consensus.

[Aquillion]

They are taking about characters/enemies with things like 'alert' that prevent them from being surprised I believe.

I don't like that it is technically possible for a character that is ambushed and doesn't see the enemy yet to act before then, but technically it is RAW. I suggest anyone else that dislikes that rule to houserule that being the surprising force gives an automatic Nat 20 initiative roll (first round only. Follow their natural initiative roll starting in round 2) It still allows for someone with massive bonuses to act before their ambusher, but other then builds that are super focused on this it should rarely if ever allow an ambushed character to act before the ambusher.

The first time I clashed with this RAW the party walked near a tower that had archers hiding up top to ambush them. Someone with alert rolled higher initiative and I foolishly allowed them to attack (and kill) an ambusher that they shouldn't have been aware of yet. I discussed with my players and made modifications after that incident with table consensus.

No, that's not true. A character who is ambushed gets no action on their first turn. Read the surprise rules I quoted above more carefully.

By my strict reading of the rules, your example should have worked like this:

1. Was the archer "trying to be stealthy?" If not, they're noticed automatically.

2. If they were trying to be stealthy, they roll a Dexterity (Stealth) against everyone's passive perception. Anyone who fails is surprised and misses their entire turn in the first round. They technically roll initiative, but they don't get to attack and kill anyone.

Note that by RAW, failing to notice even a single enemy combatant puts you in surprised status and causes you to miss your entire first turn. That is to say, if there were six archers in the tower, every one of them rolls Dexterity (Stealth); to avoid being surprised, your passive perception has to beat all of them. Fail even one, and your first turn gets skipped.

The rules are really clear, so I'm not sure what point you're confused about:

Otherwise, the GM compares the Dexterity (Stealth) checks of anyone Hiding with the passive Wisdom (Perception) score of each creature on the opposing side. Any character or monster that doesn’t notice a threat is surprised at the start of the encounter.

If you’re surprised, you can’t move or take an action on your first turn of the combat, and you can’t take a Reaction until that turn ends. A member of a group can be surprised even if the other members aren’t.

Everyone who's trying to hide gets to roll Dexterity (Stealth) against passive Wisdom (Perception). And anyone whose Wisdom (Perception) is beaten by anyone in that check misses their entire first turn.

(I think it's intentionally set up in a way that lets one rogue on an otherwise unstealthy party feel awesome by putting all the enemies in a surprised state.)

With our example character, they have Expertise in Stealth and Pass Without Trace, so at level 9, assuming they have +2 from Dex (reasonable even for the Hexblade-version, since it's still useful to them), even if they roll a natural 1, anyone with 20 or lower passive perception will be automatically surprised and miss their first turn, regardless of their initiative result (if they roll poor initiative, they could even get assassinated twice, although the Gloom Stalker ambush won't apply on round 2.)

Also it's worth pointing out that they get both +Dex and +Wisdom to Initiative, and advantage on Initiative due to being a Ranger. So they're extremely unlikely to lose initiative in the first place.

[Galithar]

No, that's not true. A character who is ambushed gets no action on their first turn. Read the surprise rules I quoted above more carefully.

By my strict reading of the rules, your example should have worked like this:

1. Was the archer "trying to be stealthy?" If not, they're noticed automatically.

2. If they were trying to be stealthy, they roll a Dexterity (Stealth) against everyone's passive perception. Anyone who fails is surprised and misses their entire turn in the first round. They technically roll initiative, but they don't get to attack and kill anyone.

Note that by RAW, failing to notice even a single enemy combatant puts you in surprised status and causes you to miss your entire first turn. That is to say, if there were six archers in the tower, every one of them rolls Dexterity (Stealth); to avoid being surprised, your passive perception has to beat all of them. Fail even one, and your first turn gets skipped.

The rules are really clear, so I'm not sure what point you're confused about:

Everyone who's trying to hide gets to roll Dexterity (Stealth) against passive Wisdom (Perception). And anyone whose Wisdom (Perception) is beaten by anyone in that check misses their entire first turn.

(I think it's intentionally set up in a way that lets one rogue on an otherwise unstealthy party feel awesome by putting all the enemies in a surprised state.)

With our example character, they have Expertise in Stealth and Pass Without Trace, so at level 9, assuming they have +2 from Dex (reasonable even for the Hexblade-version, since it's still useful to them), even if they roll a natural 1, anyone with 20 or lower passive perception will be automatically surprised and miss their first turn, regardless of their initiative result (if they roll poor initiative, they could even get assassinated twice, although the Gloom Stalker ambush won't apply on round 2.)

Hi brick wall. Instead of posting irrelevant walls of text, try reading the Alert feat that literally says YOU CANNOT BE SURPRISED while concious period. And then try to argue again. You'll notice that is a character with alert is attacked initiative must be rolled, and as they can act on their first turn by not being able to be surprised they can RAW act before their ambusher.

Note: You clearly didn't read what I wrote, so I didn't read what you wrote.

Edit: Your twisting of the rules also gives entire parties the advantage of stealth if only one person is unnoticed, which you might think it's cool, but wait until the 7 Giants get to hit you in a surprise state because they have one small buddy hiding behind them that pops out and goes 'boo' making your entire party lost their first turn.

[bid]

regardless of initiative

You can still fail to act first once in a while.

Huh?
Surprise is a thing in 5e, even if it's not formally called a "surprise round."

Assassinate advantage ends as soon as you take a turn, which is the "first turn" whether you are surprised or not. Even if "take a turn" only gives you back your reaction.

[Meichrob7]

One little hiccup.

When you sneak attack you have to roll initiative. So if your target beats your roll, you do not auto crit.

Right and I can't speak from a ton of experience with the level 20 build because I only ran that once in a oneshot, but this was actually the second character I ever played after out DM overbuffed the pudding king fight and wiped half the party. At level 7 he was rocking +5 from alert, +4 from 18 Dex, and +3 from wis. You wont always go first but you usually will. Since a lot of DnD fights will hover around 3 enemies then theres a pretty damn good chance you'll go before at least one person and they'll be surprised.