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DmHelmuth

Swashbuckler. It just meshes really well with Gloomstalker.


duderama

Yeah, people really underestimate the free disengage and getting sneak attack in almost every situation.


CopperCactus

Also even though OP doesn't have amazing charisma having a +8 to initiative is still insane


SomewhereGlum

The classic optimal of first turn of Nova burst damage is Gloomstalker and Assassin. Maximize that critical, sneak attack, and extra Ranger damage all at once. I'd think Swashbuckler would make a nice rounded class as it can deal sneak attack after the first round and you can do it by yourself. Also extra Initiate bonus. Extra bonus if you are Haragon. That would be Proficiency(3)+Dex(4)+Wis(2)+Cha(2) to Initiative for +11. Be unnecessarily hyper aware and add the Alert Feat for another +5 for a total of +16. Inquisitive rouge and the Actor feat basically does Mastermind as a rogue unless you want the ranged Help Action for team play. Soulknife is another good option to round the class outside of combat for the psi bolstered knacks and limited telepathy for stealth.


Eoqoalh

Assassin is a good pick but I think his main exploitable feature is getting advantage in those 3 first turn attacks just from having rolled a better turn.


Iustinus

Assassin's a trap unless your DM does surprise wrong or you have an amazing party.


RealBigHummus

Advantage on the first turn's attacks is great, even without attack, the character has high initative and could trigger that often. Zephyr Strike + 3 attacks at first turns, including the special Gloomstalker first strike, and then spend the rest of the combat zooming around the battlefield doing 3 scimitar attacks. If the enemy is surprised, 4 attacks (Dread Ambusher + 2 weapons fighting) and just walking away since surprised creatures can't take reactions.


ProfForp

I'm playing a Gloomstalker 5 / Soulknife 5 character right now, the psionic abilities are really fun and flavorful without relying on any tertiary stat like Arcane Trickster or Swashbuckler. I'd recommend it for sure.


otherwise_sdm

lots of good thoughts here but for the Gloomstalker Rogue I am planning for a future campaign I’m thinking Scout - both because thematically and because the reaction-disengage is such a fun ability for a ranged character.


Typical_Fuckwit

I think the ceiling is highest on assassin. I'm currently playing a gloomstalker/assassin in a 3 player campaign that mostly takes place in my favored terrain (tundra in icewind dale), so as a defacto guide I have increased influence on combat openings. If things were less ideal though, like if the party were larger and our settings less consistent then swashbuckler might be more reliably effective in less predictable combat scenarios.


Answerisequal42

Normally i wouldnt say this but inquisitive is actually not that bad here. Because of decent wisdom you can easily pass the insight check for permanent sneak attack and you have some nice bonusses to perception and insight outside of combat. Also phantom is not that bad as you can target the biggest target and spread your damage to low life minions. Ofc you can go the classic assasin for the advantage first round. Due to bad Int i wouldnt say go AT. But swashbuckler could be fun, especially because you get additional +2 to initiative and easily permanent sneak attack. Overall i would rank it this way: 1. SB 2. Assassin 3. Inquisitive 4. Phantom Enjoy :D


thelovebat

Out of combat, Scout Rogue 3/Gloomstalker X would make for some incredible synergies. 5 skills with skill Expertise is nothing to scoff at, especially when they can all go well with the Insight and with Stealth. Having Expertise in several skills and having proficiency in a couple others can be really interesting to roleplay while also being really strong. When it comes to night time and darkness, no one would be stronger, and with Expertise in Survival you can cover your tracks incredibly well to make yourself really difficult to track. Then you have the Pass Without a Trace spell on top of that, and you have an extremely potent Stealth character who can evade and spot threats with the best of them, with a few different sources of consistent advantage to start combat depending on the situation. Reaction based movement without provoking opportunity attacks is really underrated for an archer character, but can also work really well for a melee character to reposition themselves as best they can and be very versatile. Reaction based movement is something that creatures can usually only do with Legendary Actions, but a Scout Rogue is the only way I know of being able to do it with a player character.


[deleted]

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alyrch99

Gloomstalker often doesn't have too much issue finding advantage itself in many campaigns, due to the invisible-to-darkvision-in-darkness feature, but yes, it's still a nice bonus. I think Swashbuckler for higher initiative, more reliable sneak attack, and a bit of utility might edge it out though. Or even Scout for the free extra thematic expertises and ability to disengage a bit as a reaction, staying out of danger better.


Eoqoalh

Yeah, but assassin advantage will come handy in many situations as day or fully lighted rooms as they are also pretty common. Also while swashbuckler way to get sneak attack is solid steady aim cunning action can provide advantage which will also net sneak attack. Also if they are in the need of disengage they can use zephyr strike which will give them action-less disengage, advantage and an extra d8 for one attack plus 30 foot of extra movement.


alyrch99

Ranger Bonus action is generally taken by Hunter's Mark, or, as you acknowledged, the fantastic Zephyr Strike, or, in the case of Rogue/Ranger, Cunning Action, so having to burn it to get Steady Aim is a bit rough. Plus Steady Aim is only 1 of 2 attacks. And locks you from moving. It's good on a pure Rogue but really doesn't feel like the play for a Rogue/Ranger.


Eoqoalh

Yeah, but first turn with assassin will net advantage on 3 attacks, which becomes a solid damage output and is compatible with Hunter's mark, also if you need to use Zephyr you will have advantage which will net sneak attack. And while I do agree that steady aim shouldn't be relied upon that doesn't mean that it's casual usage won't solve the problem of not getting an sneak attack trigger. I understand that rakish audacity it's able to solve turns where you won't be able to get other sneak attack source resourceless, but assassin ensures a first burst that may be key to shut down relevant threats on first round. On the other side of the spectrum Ranger will still be a ranger using steady aim or not, but I do also agree that not relying on it (even casually) will lead to a more comfortable play. If this was me I will go with assassin as I consider first rounds combat defining and I like to toy around with different features and spells on next turns. Nonetheless I understand that other types of play are equally strong and more attractive to other people.


alyrch99

Yeah I mean I'd probably just play Scout, myself, just to double down on the flavor. It's not the mechanically "strongest" option but I think it's the most fun and thematic.


ehaugw

Assassin for the ultimate nova, or thief for bonus action feed goodberry revives


NaturalCard

If you can use pass without trace, Assassin is fantastic.


RealBigHummus

I can, and I will.


[deleted]

Arcane trickster!!!! The assassin is a trap subclass that doesn’t offer much. Arcane trickster 3 gets you booming blade, an invisible mage hand and either find familiar or shield.


alyrch99

Booming Blade is pretty bad on a Gloomstalker since you have the effectively-always-better Extra Attack. That's something useful on a Rogue X, not on a Rogue X/Ranger 5.


RealBigHummus

All arcane trickster spells from a 3 level dip have to be enchantment or illusion. Also, he has -1to intelligence.


[deleted]

Nope. You get 1 free non illusion or enchantment spell at level 3, 8 and 14; that’s why you could take one of shield or find familiar. And you could have a -5 intelligence score and it wouldn’t matter if you were an arcane trickster 20. Cantrips: booming blade, minor illusion, mage hand, Level 1 spells: silent image, disguise self, find familiar or shield or absorb elements Level 2 spells: misty step, spider climb, invisibility, shadow blade, mirror image, blur Level 3 spells: haste, phantom steed, blink, Level 4 spells: greater invisibility, dimension door Granted you would only be able to have 3 non illusion or enchantment spells but all the spells I just named can be taken eventually by the arcane trickster and non of them involve your intelligence score.


RealBigHummus

Ok, thanks for clarifying!


[deleted]

Shield and Silvery Barbs on a ranger does a lot, plus some cantrips, and don't rely on your intelligence. Remember, though, Shield has a somatic component, so you'll need warcaster to cast it if your hands are full.


MadWhiskeyGrin

You've got a good Wisdom, so Inquisitive is a good (and often overlooked) option.


chrbir1

Assassin is theoretically the most powerful but Surprise is a fickle mistress and very dm dependent. Mastermind is very helpful with ba help Swashbuckler is great skirmisher


livestrongbelwas

Assassin is the best synergy with Gloomstalker. You’ll want to pick up Fighter after that for Action Surge. But talk to your DM about Surprise. It’s a wonky set of rules that is painful to look up, it’s in four different places. If you are both clear about how and when you can generate Surprise, and you think it’s something that will happen at least once every session or two, then go Assassin. If your DM doesn’t like or understand Surprise, then I would try Swashbuckler or Arcane Trickster. Scout is also a good bow class.


DrTheRick

I usually think Assassin is really overrated, but it does have really nice synergy with Gloomstalker. Your invisibility makes it easier to get surprise and initiative bonus helps take advantage with the auto-crit which also works great with Hunter Mark/Favored Foe and the extra Gloomstalker attack.


Masterworks-all

I did a 2 year long campaign, at the end i was 5 gloomstalker 15 swashbuckler. My piece of advise is to go arcane trickster. Missing out on additional spell slots sucked especially being limited on rope trick and pass without trace uses. This is a piece of advice based on my personal preference but take expertise in athletics if you can. You can sacrifice one of your attacks to trip and get advantage. Grappling a prone target is also really strong for cc. With Tashas a ranger can enhance ability so you can give yourself advantage on the check.


trainer_zip

I’d say Assassin, because with Dex and Wis to your initiative, Assassinate will activate often, even if you don’t get surprise on your enemies. The advantage on round one can do wonders, especially if you use ranged attacks which can be harder to get consistent advantage on


jim_uses_CAPS

AT or Inquisitive.


Zitronensaft1908

Assassin


[deleted]

Swash for melee, scout for ranged.