Is it too late?

[FaceofBo]

Hey Playground, i am currently knee-deep in a campaign as a Tabaxi Ranger, and i was thinking of either dipping into monk/going monk levels. I know Ranger is pretty bad rm, and I was hoping to shore up some of my defenses//weaker parts of my character with levels in Monk. The only problem is I'm not sure when to do it/how many levels to take. I'm level 3 currently, about to hit 4, and I was heavily debating taking monk levels. My reasoning being it's SAD as heck, if I go into Kensai I can kinda go down the Bow Master thematic, or go Shadow Monk to match my Gloomstalker, but I am still unsure, and just looking for some advice/opinions.

-Thanks in advance

[Spore]

That depends on your wisdom score mostly. If you're a dex ranger with Wis of 14+, I'd say go ahead.

[thoroughlyS]

Definitely wait until 6th level. Getting Extra Attack at 5th is important for every martial character.

[ImproperJustice]

I have seen Ranger 6 / Druid x work as a favorable combo. Now, that was using Revised Ranger, but it provided a nice mix of martial and magical power.

[Foxhound438]

Definitely wait until 6th level. Getting Extra Attack at 5th is important for every martial character.

you can kind of get away with it going into monk though, since you do get the second attack from martial arts.

Whether to and when to multiclass for you is really going to depend on the expected length of your campaign. If you expect to have the game stop around level 7-9, you might be better off sticking pure ranger, or at least get ranger 5 first. Regardless of where the game ends exactly there, you definitely want to get extra attack, and you don't start seeing the really boring levels (sans 6th) until later on in ranger anyways.

If the campaign is expected to get to levels 10+, going for some monk or rogue levels is ultimately probably the best choice. I would say if you know the character is going to get high level, you should go ahead and start taking monk levels immidiately. It might be a bit harsh not having extra attack until level 8, but between ranger and kensai abilities, you have pretty close to the damage that sneak attack would give a rogue for the few levels you're off anyways.

If it's up in the air as to whether or not you'd get to high levels, maybe get ranger 5 and start taking rogue levels instead for more free damage.

[ProsecutorGodot]

I would recommend fighter over monk and rogue over fighter.

Monk - Shadow Monk synergizes very well with Gloomstalker, no Longbow martial arts unless you take Kensei though. You also can't wear armor for a lot of class abilities to work. There's a bit of redundancy involved with Shadow Monks skills as a Gloomstalker you don't get the really useful stuff without a 6 level investment.
Fighter - Fighter is just great in general, Second Wind is a decent heal and Action Surge is pretty incredible. Take it to Battle Master or Samurai and you can really cause some havoc. Almost every class benefits from a dip into fighter.
Rogue - Skill proficiencies, Sneak Attack, Cunning Action. Take it to 3 for Assassin or Scout. Assassin pairs great with your bonus to initiative from Gloomstalker and Scout can make sure you're never pinned down by someone getting in your face. It's also worth noting that Thief is useful for keeping the high ground as an archer and fast hands is a criminally underrated skill.

They're all good options but Rogue (and Fighter to a lesser extent) does a lot more for combat effectiveness, Rogue has the added benefit of giving you maneuverability and ,at later levels, survivability to match.