Greetings all.

I've been investigating the Gloomstalker Ranger...and man, those are some nice features.

You become invisible to creatures with Darkvision in total darkness...you get a bonus to your inititative equal to your Wisdom modifier...and you get an extra Attack at the beginning of combat, with bonus damage, to boot!

Some additional digging has informed me that a multiclass with Rogue, then, becomes even better...you quite literally become a Dread Ambusher, taking enemies by surprise and getting additional opportunities to Sneak Attack.

My plan is to take Gloomstalker to either Level 3 or 5, and put the rest into Rogue.

My indecision is which Rogue subclass to choose to go with Gloomstalker.

For the character, they are going to be a Ghostwise Halfling...healthy boosts to Dexterity & Wisdom...plus, they can telepathically speak into the minds of targets.

In those situations where the halfling with be invisible to enemies..I fully plan on using psychological warfare to whisper dissent among their ranks.

As a concept, I'm going to make this halfling a parody of Rambo...a pint-sized, traumatized veteran of war who terrorizes his enemies through traps & ambushes.

...which brings me to the Rogue subclasses:

Scout Rogue seems to be a popular choice...the free "Expertise" in Nature and Survival is certainly on-theme for a Halfling-Rambo...but I'm a bit iffy on the other features. For a bow-&-arrow Halfling Rambo, this is solid.

Thief Rogue has slowly become more favorable to me, what with their "Fast Hands" being great for triggering traps or other situational benefits, while retaining some of the movement bonuses of the Scout...and all the other skill compliment a Gloomstalker wonderfully, granting them advantage on Stealth checks, using Magical items, and (while unlikely), the Thief capstone makes Dread Ambusher utterly bonkers. For a throat-cutting, trap-making Halfling Rambo, this seems like a lot of fun.

Swashbuckler Rogue provides a solid combat boost to the character after they make their ambush...and the initiative boost from a Charisma-modifier, PLUS the Wisdom-modifier seems a bit ridiculous....add the "Alert" feat to the mix, and it's like this Halfling will always be going first.

Inquisitive Rogue is interesting...the Wisdom stats couple well with the Inquisitive features...but I'm not sure if the subclass is very on-theme for an ambusher. Perhaps someone can offer some good "flavor" for such a multiclassing.

Finally, the Assassin Rogue really helps maximize the first surprise attack of combat...adding both advantage AND a critical hit if the target is surprised.

Now....the target has to be "surprised" for the bonus damage...and a Gloomstalker certainly provides more chances of this happening...but I like a bit of versatility in my subclass features, and the Assassin somewhat lacks this.

Anyway...that's my subclass-paralysis.

Anybody have some thoughts on what Rogue subclass pairs best with a Gloomstalker Ranger?

Quote from Tony1Adobe >>

and you get an extra Attack at the beginning of each round of combat, with bonus damage, to boot!

This may influence your decision - but the extra attack only happens on the first round of combat - not subsequent rounds. But - it works per Attack action so Action Surge from a Fighter will give you another one if you use it on your first turn.

Quote from Emmber >>

Quote from Tony1Adobe >>

and you get an extra Attack at the beginning of each round of combat, with bonus damage, to boot!

This may influence your decision - but the extra attack only happens on the first round of combat - not subsequent rounds. But - it works per Attack action so Action Surge from a Fighter will give you another one if you use it on your first turn.

 Whoops.

I knew that, but it seems I failed to write it that way. 

Fixed.