Help Needed on Hiding During Combat

[AHF]

Bringing this over from the RAW thread and adding a couple notes for organization:

Questions on Hiding During Combat

Sorry if some of these are elementary but I am a relative newbie trying to DM a party with a Half-Elf Paladin and Halfing Rogue. The 3rd Level Arcane Trickster Rogue uses his cunning action most rounds to hide behind the Paladin. He looks to attack with advantage and sneak attack every round either with a ranged weapon (bow or crossbow) or melee weapon (rapier or short-sword). I've read the rules on stealth and a couple threads but feel like I really don't have a great grasp on it yet.

BASIC HIDING

#1 When the Halfing hides and is in position to get cover from the Paladin, am I supposed to use the stealth roll of the Halfing in a contest versus a perception check of the enemy or use the passive perception of the enemy? With expertise in stealth, it is super easy for the Halfing to beat an enemy's passive perception. I assume that for opponents where the Paladin does not provide cover that the Halfing can't hide.

Example: Hallway with X = Walls, E1 = Enemy 1, P = Paladin, H = Halfing, E2 = Enemy 2

XXXXXXXXXXXXXXXXXXXXXXXXXXXXXXX
E3 ------ E1 ------ P H ----------- E2
XXXXXXXXXXXXXXXXXXXXXXXXXXXXXXX

So contest with H's stealth versus E1 perception and E3 perception and no contest with E2? Passive perception for E1 and E3?

BASIC COMBAT WHEN HIDDEN

#2 If the Halfing successfully hides, will he get advantage and sneak attack when attacking E1 or E3 with a ranged attack if the Paladin is not within 5 feet of E1 yet?

#3 If the Halfing successfully hides, can he be targeted by E1 or E3 casting spells with an attack roll at disadvantage (like Firebolt)? Can he be targeted by E1 or E3 by spells without an attack roll (like Hold Person)? Does this depend on whether the spell calls out a need to see the target? (I.e., hold person says a target you can "see" but firebolt just says a creature "within range")

AT WHAT DISTANCE DOES HIDING TAKE PLACE WHEN ALLY IS IN MELEE?

#4
XXXXXXXXXXXXXXXXXXXXXXXXXXXXXXX
E3 ------ E1 P H ------------------- E2
XXXXXXXXXXXXXXXXXXXXXXXXXXXXXXX

If the Paladin and E1 are engaged in melee and E1 is using a melee weapon like a longsword with 5 foot range, can the H hide and stay >5 feet back from E1 and then pop out and use a ranged attack at advantage versus E1 and then go back into hiding without drawing an attack of opportunity? (I know sneak attack applies since the Paladin and E1 are engaged in melee but am wondering about the 5 foot disadvantage for ranged attacks and wondering he can hide while remaining further than 5 feet out while still getting the benefit of hiding). If not, is the attack normal (i.e., disadvantage from being at close range canceling out with the advantage from hiding) while still getting the sneak attack due to proximity of E1 and P? If he can't stay >5 feet away does he get to rehide without avoiding an AOO since he stays within 5 feet?

#5 If the Paladin and E1 are engaged in melee, can the H pop out and stab E1 with a melee weapon and use his cunning action to hide without drawing an attack of opportunity? (This is perhaps just a variation on 477(d) and trying to clarify that if he can't hide while being >5 feet away, can he stay within 5 feet and hide without drawing an AOO?)

DOES THE RANGED DISADVANTAGE PENALY APPLY IF ROGUE IS HIDDEN FROM NEARBY OPPONENT?

#6 If the answer to 477(d) is that he can't both hide and avoid being within E1's melee range if he wants to hide behind P, can he pop out and shoot at E3 with advantage instead of trying to shoot E1 at close range or does being within 5 feet of E1 still impose disadvantage even when he is hidden from E1?

CAN A HALFING HIDE USING AN OPPONENT?

XXXXXXXXXXXXXXXXXXXXXXXXXXXXXXX
E3 ------ E1 H -------------------
XXXXXXXXXXXXXXXXXXXXXXXXXXXXXXX

#7 Can the Halfling hide from E3 behind opponent E1? (I.e., if E1 is attacking him with a longsword can H swing at E1 and use cunning action to position himself behind E1 to gain hidden status vis-a-vis E3?)

#8 If so, what if the Halfing attempts to hide behind an enemy with a 10 foot reach? Using the example above, can the Rogue hide behind E1 who is attacking him with a halberd (or some other weapon with 10 foot reach) to gain advantage on a ranged attack against E3 by moving 6 feet from E1, shooting E3 and then hiding behind E1 again without provoking an AOO since he never left E1's reach?

Many thanks in advance.

[Easy_Lee]

You're making this more complicated than it needs to be.

Naturally Stealthy: You can attempt to hide even when you are obscured only by a creature that is at least one size larger than you.

Thus the halfling can hide behind anyone larger than him, even an enemy, as long as that creature is between him and what he's trying to hide from. Picture it like hiding behind a tree.

When hidden, the halfling cannot be seen. Thus he cannot be the target of attacks or spells that require a target if he is hidden from the attacker. This also applies to his allies, by the way. He hides from them too.

The halfling attempts to hide using his stealth check vs passive perception. He's hidden from anyone whose passive perception he beats until he reveals himself, they move into a position that allows them to see him clearly, or they make an active perception check (action) that beats his stealth check. This is one reason why hiding in a backpack is so effective for small rogues; enemies can't see you no matter where they stand, and the backpack's material might provide cover.

The halfling reveals his position when he makes an attack. He has advantage on the attack since he's hidden when he makes the attack. The common ruling is that rogues can poke their heads out of hiding and make one attack while still hidden. The book isn't completely clear on this but it seems to be the intent.

[AHF]

You're making this more complicated than it needs to be.

Naturally Stealthy: You can attempt to hide even when you are obscured only by a creature that is at least one size larger than you.

Thus the halfling can hide behind anyone larger than him, even an enemy, as long as that creature is between him and what he's trying to hide from. Picture it like hiding behind a tree.

When hidden, the halfling cannot be seen. Thus he cannot be the target of attacks or spells that require a target if he is hidden from the attacker. This also applies to his allies, by the way. He hides from them too.

The halfling attempts to hide using his stealth check vs passive perception. He's hidden from anyone whose passive perception he beats until he reveals himself, they move into a position that allows them to see him clearly, or they make an active perception check (action) that beats his stealth check. This is one reason why hiding in a backpack is so effective for small rogues; enemies can't see you no matter where they stand, and the backpack's material might provide cover.

The halfling reveals his position when he makes an attack. He has advantage on the attack since he's hidden when he makes the attack. The common ruling is that rogues can poke their heads out of hiding and make one attack while still hidden. The book isn't completely clear on this but it seems to be the intent.

That helps a lot.

So when the Halfling emerges from hiding and stabs someone there is no AOO when they use cunning action not to disengage but to re-hide?

(If the Halfling is hiding in a backback can't an opponent just target the backpack? That seems similar to pulling a normal blanket over yourself on the battlefield.)

[AHF]

With the passive perception is this correct?

Level 20 Cleric with 20 Wisdom = 15 Passive Perception (10 + 5 for Wisdom Modifier)

Level 3 Rogue with 16 Dex and Expertise In Stealth = 1d20 + 3 + 2x2(Prof Bonus) = 1d20 +7. Requires a roll of 9 to hide successfully.

[Easy_Lee]

That helps a lot.

So when the Halfling emerges from hiding and stabs someone there is no AOO when they use cunning action not to disengage but to re-hide?

(If the Halfling is hiding in a backback can't an opponent just target the backpack? That seems similar to pulling a normal blanket over yourself on the battlefield.)

Regarding attacking the backpack, yes. The rogue might even count as restrained in that case. Hopefully your players won't get clever and craft an adamantine backpack.

The halfling won't provoke attacks of opportunity while he's hidden but he may not be able to get to a spot the opponent can't see in order to hide if the opponent is close enough to hit him, unless the opponent has long reach. Example, line breaks are five feet:

G = Giant
H = Human paladin
R = Lightfoot halfling rogue

The paladin is concealing the rogue from the giant so the rogue can hide and then, if successful, move out of the giant's reach without provoking an attack of opportunity.

With the passive perception is this correct?

Level 20 Cleric with 20 Wisdom = 15 Passive Perception (10 + 5 for Wisdom Modifier)

Level 3 Rogue with 16 Dex and Expertise In Stealth = 1d20 + 3 + 2x2(Prof Bonus) = 1d20 +7. Requires a roll of 9 to hide successfully.

Unless the cleric has the Perception skill, the above is correct. If the cleric does have perception then it will be 21 (10+5+6). If the cleric also had observant then it would be 26. While I'm at it, an inquisitive rogue who's pushing it might get his passive perception up into the 30s.

[DivisibleByZero]

The paladin is concealing the rogue from the giant so the rogue can hide and then, if successful, move out of the giant's reach without provoking an attack of opportunity.

Only if he can remain hidden from the giant while moving out from behind the paladin, which is doubtful. The instant he steps out from behind the paladin, he is no longer hidden, not from the giant or anyone else who has line of sight on him.
And anyone who had line of sight on him while he was behind the paladin (like his party members, probably) would have known where he was the entire time (unlike what you said before about hiding from his party).
You're only hidden if they can't see you. You can be hidden from person A and not be hidden from person B, both at the same time.

[Easy_Lee]

Only if he can remain hidden from the giant while moving out from behind the paladin, which is doubtful. The instant he steps out from behind the paladin, he is no longer hidden, not from the giant or anyone else who has line of sight on him.
And anyone who had line of sight on him while he was behind the paladin (like his party members, probably) would have known where he was the entire time (unlike what you said before about hiding from his party).
You're only hidden if they can't see you. You can be hidden from person A and not be hidden from person B, both at the same time.

Right. The paladin can see him but he isn't hidden from the giant anymore if he moves back and the giant can see over the paladin. However, he is still hidden from anyone behind the giant. The hide action doesn't require you to specify who or what you're trying to hide behind.

A ruler or similar is useful to make straight lines and determine who can see who.

[AHF]

Only if he can remain hidden from the giant while moving out from behind the paladin, which is doubtful. The instant he steps out from behind the paladin, he is no longer hidden, not from the giant or anyone else who has line of sight on him.

So the moment he steps out from behind the Paladin, does he get advantage on the attack if the target has line of sight?

Does the enemy get an opportunity attack when he retreats behind the Paladin again without using disengage?

(I'm not too fixated on the Giant scenario which seems more concerned with the issue of whether the Giant has line of sight behind the Paladin due to his size - for purposes of this I am assuming he can get concealment behind the Paladin in an effort to understand routine hiding and rogue attacks)

[Easy_Lee]

Targets are no longer hidden as soon as the enemy in question has line of sight to them. Regarding opportunity attacks, stepping into a foe's reach does not normally trigger.

[DivisibleByZero]

So the moment he steps out from behind the Paladin, does he get advantage on the attack if the target has line of sight?

Does the enemy get an opportunity attack when he retreats behind the Paladin again without using disengage?

(I'm not too fixated on the Giant scenario which seems more concerned with the issue of whether the Giant has line of sight behind the Paladin due to his size - for purposes of this I am assuming he can get concealment behind the Paladin in an effort to understand routine hiding and rogue attacks)

Adv: Yes, because he was hidden. Think of it like someone jumping out from behind a door and scaring you. Even if you had an idea that they were there, you didn't know exactly where they were or exactly when they'd jump out and scare you.

OA: Yes, because he is no longer hidden. Unless he hides again, and can remain hidden until he's out of the giant's OA range. If he moves into a space where he is no longer hidden, then he's just moving in the open and is subject to everything that would normally happen to anyone else openly moving to/from that space.

[BlackbirdXX]

I think the other small piece maybe being overlooked is cover and space? As I DM I felt like the Halfling rogue was an easy button until I stopped adding assumptions or rational that aren't in the rules.

So in the hallway example... yes. He can make a ranged attack with advantage against E1 and E3 but P grants E1 1/2 cover and you could argue P + E1 grants E3 3/4 cover. E3 can clearly see him so he should figure that problem out first. :)

As for melee, in the same hallway example... he doesn't have reach to hit E1. He can move through a friendly square but can't 'end' there, even transitionaly to attack. And once he leaves the 'obscurement' provided by P, he is no longer hidden. So he can't just hide and then walk invisible up to E1 and stab him. The minute he advances past P he is no longer obscured.

And once E1 engages P, melee becomes impossible for the H (unless reach, whip maybe).

[Armored Walrus]

Note that AoO requires that you see the target. So you can be not hidden and still not suffer an opportunity attack if the attacker can't see you. So you could Hide behind the paladin, attack w opportunity, move back behind the paladin, NOT HIDE, and still move away without an AoO as long as you never get within line of sight of the giant. It being a giant, though, I would rule that as soon as the halfing takes one step straight back, the giant can see him over the paladin's head. But, not to get bogged down in that specific example (I know, too late) Hidden means those you've Hidden from don't known where you are and can't see you, broken line of sight just means they can't see you. There are different mechanics affected by those two different statuses.

[DivisibleByZero]

Note that AoO requires that you see the target. So you can be not hidden and still not suffer an opportunity attack if the attacker can't see you. So you could Hide behind the paladin, attack w opportunity, move back behind the paladin, NOT HIDE, and still move away without an AoO as long as you never get within line of sight of the giant. It being a giant, though, I would rule that as soon as the halfing takes one step straight back, the giant can see him over the paladin's head. But, not to get bogged down in that specific example (I know, too late) Hidden means those you've Hidden from don't known where you are and can't see you, broken line of sight just means they can't see you. There are different mechanics affected by those two different statuses.

What?

I was about to write a long post arguing this, but then I realized that it was a waste of my time, and would likely just devolve into an endless argument.
So never mind. Carry on thinking that you can stand directly in front of an enemy after revealing yourself by attacking, not attempt to hide, and somehow still not be seen.

[Easy_Lee]

Note that AoO requires that you see the target. So you can be not hidden and still not suffer an opportunity attack if the attacker can't see you. So you could Hide behind the paladin, attack w opportunity, move back behind the paladin, NOT HIDE, and still move away without an AoO as long as you never get within line of sight of the giant. It being a giant, though, I would rule that as soon as the halfing takes one step straight back, the giant can see him over the paladin's head. But, not to get bogged down in that specific example (I know, too late) Hidden means those you've Hidden from don't known where you are and can't see you, broken line of sight just means they can't see you. There are different mechanics affected by those two different statuses.

That's a good point. Attacks of opportunity don't go off if you manage to conceal yourself in some way. By the same token, anyone should be able to step behind a tree or similar and be un-targetable by spells that require line of sight if the caster doesn't have LOS.

[Armored Walrus]

Naturally Stealthy: You can attempt to hide even when you are obscured only by a creature that is at least one size larger than you.

He's not directly in sight of the giant. He's obscured by a creature one size larger. Line of sight rules are independent of Hide rules. The only place they intersect is you have to be obscured (no line of sight) in order to attempt to Hide.

Same way and Invisible creature can move away without an AoO. You have to see the target of an AoO. So even though the Invisible creature is not hidden (ie. folks know what square it's in) it can't be attacked with an AoO.

Again, didn't want to get bogged down in the details of that specific example. Just pointing out that not having line of sight on a creature is different than that creature being hidden.

[BlackbirdXX]

I think I follow what you are saying. If it were a terrain feature instead of your ally that was hiding you it would make more sense.

But I thought any attack, successful or not, basically nullified hidden. So If you hide under a small stack of crates... reach out and sneak attack his tendon... you kinda give yourself away but still can't be targeted? You are no longer hidden but still obscured so no OoA? Of course OoA happens when you move out of his reach, so better hope the crates are piled longways. :)

[Easy_Lee]

I think I follow what you are saying. If it were a terrain feature instead of your ally that was hiding you it would make more sense.

But I thought any attack, successful or not, basically nullified hidden. So If you hide under a small stack of crates... reach out and sneak attack his tendon... you kinda give yourself away but still can't be targeted? You are no longer hidden but still obscured so no OoA? Of course OoA happens when you move out of his reach, so better hope the crates are piled longways. :)

You are no longer hidden if you attack but you might still be unseen. Classic example is the devil's sight warlock attacking from darkness.

[Armored Walrus]

I think I follow what you are saying. If it were a terrain feature instead of your ally that was hiding you it would make more sense.

But I thought any attack, successful or not, basically nullified hidden. So If you hide under a small stack of crates... reach out and sneak attack his tendon... you kinda give yourself away but still can't be targeted? You are no longer hidden but still obscured so no OoA? Of course OoA happens when you move out of his reach, so better hope the crates are piled longways. :)

Have to see a target to get an AoO on it. Hidden or not. So yeah, the attack means you're not longer hidden, but if you can break line of sight somehow before moving out of reach, no AoO. Not sure how I'd rule in your specific example, but the rule itself is that you must be able to see your target in order to AoO them.

Note that being able to melee attack from hiding is considered by some folks here to be an edge ruling as well. In order for you to stab your opponent from under that stack of crates, you have to have line of sight on them, and if you have line of sight on them, they have line of sight on you, so you are not hidden. I personally don't rule it that way, and in your example above I'd probably allow the attack at advantage, but also allow the AoO since the target is going to try to swipe at you while you're still visible with your dagger hand extended from the crates.

[Millstone85]

Line of sight rules are independent of Hide rules. The only place they intersect is you have to be obscured (no line of sight) in order to attempt to Hide.

Yes, a general rule is that you must be unseen before you can become hidden. And I do think that being unseen to a creature, being heavily obscured to a creature, and offering no line of sight to a creature, are all the same notion.

But then we have Mask of the Wild, which lets a wood elf attempt to hide even when only lightly obscured by natural stuff. Here, I believe, the logic is inverted. The wood elf is unseen because they are hidden. But if the attempt fails, the wood elf can not otherwise treat the light obscurement as heavy obscurement. Opportunity attacks still trigger and so on.

Same thing, in my opinion, with a lightfoot halfling's Naturally Stealthy trait. You can not declare "No line of sight!" just because there is a medium or larger creature in the way.

[Armored Walrus]

Heh, well I'm not gonna die on that hill. In the end, no matter how many posts we spend on it, we're all going to rule our way in our games.

Hopefully OP got enough food for thought to make a ruling in his.

[Easy_Lee]

Anyway, things are a little complex at times. Here's my advice, OP: whatever you do, be reasonable and be consistent. No one can fault you for those qualities.

[Armored Walrus]

No one can fault you for those qualities.

Except on internet forums.

[Easy_Lee]

Except on internet forums.

Exceptions always exist, except for this statement, and this one, and this one...

[AHF]

Anyway, things are a little complex at times. Here's my advice, OP: whatever you do, be reasonable and be consistent. No one can fault you for those qualities.

Appreciate the follow-up on this discussion. So if I'm reading right in a standard combat it would work something like this:

"The Paladin and Halfling encounter the same 2 Orcs with their Kobold Wizard friend (with 12 wisdom) from earlier who wanted to kill the Halfling for stealing their ale along with their Wizard friend. The Orcs are 30 feet away, scream at you and charge with axes raised. Roll initiative."

Initiative Order - 1H, 2 Orcs (15 HP each), 3P, 4W (15 HP)

W
O1-----------------------H
O2-----------------------P

Round 1
- Halfing (H): I fire my bow at O1 and hide behind the paladin. Misses. Hide: Rolls 1d20+7 against the Orc's 10 passive perception and must therefore roll a 4 or higher versus Orcs and a 5 or higher versus Wizard. Rolls a 7 so hidden from everyone.
- Orcs (O1 & O2): The 2 Orcs charge and both attack the paladin because they can't see H and aren't real strategic.
- Paladin (P): Attacks O1. Hits for 8 dmg.
- Kobold Wizard (W): Can't target H with Magic Missile so blasts P.


W-----------------------O1\
-------------------------O2- PH


Round 2
-Halfling: "I jump out and sneak attack O1 with my rapier." H hits with sneak attack doing 13 damage. O1 is down. "I hide with P between me and O2." (Same 1d20+7 vs 10 for O2 and 11 for W)
-Orc2: H is hidden so O2 can't target H and attacks P.
-Paladin: Attacks O2.
-Wizard: Circles around O2 so he has line of sight on Halfling and casts fire bolt at him.

-------------------W
-------------------
----------------O2-PH

Round 3
-H: Sneak attack O2 and hide from O2 behind P. Same 1d20+7 versus 10 but only a contest against O2 this time.
-O2: Attack P unless H fails stealth check.
-P: Attacks O2, taking O2 out.
-W: Casts flame bolt at H.

Round 4 (every round until end of combat)
-H: I shoot my bow at W and hide with P in between me and W. 1d20 +7 versus 11 passive perception (needs a 5).
-P: Throws a javelin at W.
-W: Can't target H so targets P.

etc.

[BlackbirdXX]

Round 2
-Halfling: "I jump out and sneak attack O1 with my rapier." H hits with sneak attack doing 13 damage. O1 is down. "I hide with P between me and O2." (Same 1d20+7 vs 10 for O2 and 11 for W)
-Orc2: H is hidden so O2 can't target H and attacks P.
-Paladin: Attacks O2.
-Wizard: Circles around O2 so he has line of sight on Halfling and casts fire bolt at him.

This is where it breaks I think.

The halfling isn't occupying the paladins square, just hidden/obscured behind him. He needs to step forward and to the right of the paladin to hit with melee in your layout above. Thus losing his obscuring source and should be instantly visible to both orcs. Now I let it slide because 'cool' and it seems like the spirit of the rule. BUT once he downs Orc 1 and worse if he doesn't, he is still in Orc 2s reach and getting back behind the paladin will draw a AoO unless he disengages thus no hiding. Make sense?

Also Round 3 and on. Don't forget to have your enemies can use tactics also. The W isn't gonna stand in the open, he can seek cover or drop prone for free thus negating advantage on the Halfling sneak attack at range.

[Malifice]

OP, you have the rub of it (in a general mechanical sense).

The halfling can move behind the Paladin, and attempt to Hide as a bonus action thanks to cunning action, and his racial trait.

If his Stealth check beats the passive perception of his target, he is hidden from that target. He gets advantage to attack rolls, and the creature doesnt know where he is anymore (so cant attack him).

This remains the case until he attacks (which reveals him after the attack is resolved, hit or miss) or they use the search action to find him, or he otherwise gives himself away.

That said, hiding is expressly up to DM interpretation and rulings. I certainly dont allow creatures to attempt to hide when its obvious where they are (no ducking into a chest, closing the lid and attempting to 'hide' while in full view of the enemy, unless you have some kind of ability to teleport to a different position while in the chest, or a secret compartment to sneak out of like a magicians assistant does).

If a creature was watching the Halfling as he ducked behind the Paladin, or a tree, or whatever, then I wouldnt allow the Stealth check to Hide at all (DC = Nope). In the chaos of battle I'd certainly allow the occasional attempt, but if he's engaged in melee, or someone is watching him intently I'd rule he cant make the attempt (or rather that he can, but the check auto-fails due to him being watched).

[Farecry]

Also, in round two the wizard, I think, is required to make an active perception check since halfling was hidden. Line of sight doesn’t? immediately break being hidden.

[Farecry]

OP, you have the rub of it (in a general mechanical sense).

The halfling can move behind the Paladin, and attempt to Hide as a bonus action thanks to cunning action, and his racial trait.

If his Stealth check beats the passive perception of his target, he is hidden from that target. He gets advantage to attack rolls, and the creature doesnt know where he is anymore (so cant attack him).

This remains the case until he attacks (which reveals him after the attack is resolved, hit or miss) or they use the search action to find him, or he otherwise gives himself away.

That said, hiding is expressly up to DM interpretation and rulings. I certainly dont allow creatures to attempt to hide when its obvious where they are (no ducking into a chest, closing the lid and attempting to 'hide' while in full view of the enemy, unless you have some kind of ability to teleport to a different position while in the chest, or a secret compartment to sneak out of like a magicians assistant does).

If a creature was watching the Halfling as he ducked behind the Paladin, or a tree, or whatever, then I wouldnt allow the Stealth check to Hide at all (DC = Nope). In the chaos of battle I'd certainly allow the occasional attempt, but if he's engaged in melee, or someone is watching him intently I'd rule he cant make the attempt (or rather that he can, but the check auto-fails due to him being watched).

Do you let your players know beforehand you don’t like the RAW stealth mechanics? I ask because I had a DM who is the same and didn’t tell me until character was in game already, which was super frustrating for me, as it was a stealth concept character. He was gracious enough to let me bring a new character in instead as he agreed his view did break the characters build (started lvl 8) into not being useful.

[DivisibleByZero]

Do you let your players know beforehand you don’t like the RAW stealth mechanics?

The RAW stealth mechanics are that the DM decides when it is appropriate for someone to hide.
There is literally no wrong answer. It is entirely, 100% DM purview/fiat.

[AHF]

This is where it breaks I think.

The halfling isn't occupying the paladins square, just hidden/obscured behind him. He needs to step forward and to the right of the paladin to hit with melee in your layout above. Thus losing his obscuring source and should be instantly visible to both orcs. Now I let it slide because 'cool' and it seems like the spirit of the rule. BUT once he downs Orc 1 and worse if he doesn't, he is still in Orc 2s reach and getting back behind the paladin will draw a AoO unless he disengages thus no hiding. Make sense?

Also Round 3 and on. Don't forget to have your enemies can use tactics also. The W isn't gonna stand in the open, he can seek cover or drop prone for free thus negating advantage on the Halfling sneak attack at range.

So with the Orcs then, hiding behind the Paladin would take the Halfing outside of the 5 foot range and provoke an AOO? If so, can the halfling do the same thing except never enter the 5 foot reach and instead shoot an arrow from his bow with advantage and rehide?

The ability to hide behind a person during combat seems the express intent of the racial ability but I'm having trouble seeing how to implement it. It seems like if the hiding spot behind the person the Halfling is hiding behind is in the 5 foot range then the Halfling can melee attack with advantage and rehide without exiting the 5 foot range and drawing an AOO and if the hiding spot is outside of 5 feet away then he should be able to do the same with a ranged weapon.