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Gloomstalker/Assassin is going to be destroyer of worlds on the first turn (and good damage afterwards). And you would want to start Ranger for the first five levels, then finish with Assassin the rest of the way.
Thief does not add much to the build, not like Assassin.
The character looks absolutely nuts and I am looking forward to seeing it in action
Basically ranged death from the shadows
As for race they more or less did away with racial bonuses aside from if it has darkvision or a bonus spell or not. (everything gets a +2 and a +1 then a skill proff)
So anything with darkvision should be fine.
To answer your specific question tho:
2 Rogue > 5 Gloom Stalker > 3 Rogue (into Assassin) > 2 Fighter (1st level Second Wind, 2nd Level Action Surge)
You do ranger 5 first to get extra attack at lvl 5. Then do the rest in assassin to get the subclass skills and better sneak attack dice.
It is just an educated guess at this point... but yeah 5 levels of ranger to get extra attack. However you can cheese an "extra attack" if you use your bonus action to offhand attack which with Thief you will get 2 bonus actions instead of 1. So if you don't care about 5 levels of Ranger, you could go:
3 Thief > 3 Gloom Stalker > 6 Thief
But the 9th level Rogue abilities aren't that great tbh... Assassin is more or less a better version of the Disguise Self spell and Thief is advantage on Stealth checks if you are moving slow. The only good 9th level Rogue ability is for Arcane Trickster and you didn't even consider that one.
Arcane Trickster is a Rogue Wizard essentially and when casting a spell while hidden, the target has disadvantage on any saving throw against the spell that turn.
You get access to all the level feats
The rogues sneak attack powerup.
Extra attack with the thief bonus action (if a weaker one but give more utility)
(I suppose you could drop a feat for an extra attack and its wouldn't drop your sneak attack damage.)
Thief>Assassin
Assassin is a one shot wonder but after that it's done. Thief gives much more utility and can potentially do more damage over all with its extra offhand attack.
Gloom stalker fixes that a little bit with its first round bonus (not depending on going first) Also getting access to hunters mark as a bonus action you can mark, hide, and sneak attack all in one round (as a thief) for super damage spikes.
I wonder if you slip in and out of combat if you get the bonuses for the gloom stalker again as if you're out of combat then stealth back in (with double dash cunning) might be a be bad due to the distance you'd have to run so maybe not.
1.) You don't need to pick a race with Darkvision like someone recommended above. Gloomstalker gets Darkvision as a class regardless of race. You'll get FARTHER darkvision if your class already had it, but it's not really necessary. Someone mentioned Woof Elf for movement - that's a great option.
2.) Assassin does NOT auto-crit first round. Assassin will only auto-crit on SURPRISE rounds. You'll get Advantage on attacks first round if you went before the enemies (you almost always will). So on fights you see ahead, you can sneak over and fire an auto-crit attack to start combat, but that's the only auto crit you get.
Thief gets an extra bonus action, which is SUPER useful. Re-casting hunter's Mark costs a bonus action, so without Thief you WILL NOT be able to Hide to utilize Sneak Attack as often. Having 2x Bonus actions is super super useful, because you will regularly need both for Hide and Hunter's Mark.
3.) There's a lot of level pathways in here that are just bad, unless you just like the RP. You want to start 5 Gloomstalker. Period. Get the extra attack. Dont go 8 rogue/4 ranger. Thats a bad move. Dont go 2 rogue/5 ranger/XXX. B-Line straight for 5 Ranger so you get multiple attacks. Then, get 4 rogue (Either thief or assassin). Then is the real choice to either finish out ranger or rogue.
You either want to go 5 Ranger/4 Rogue/3 Ranger (This will give you all 3 ASI) OR 5 Ranger/7 Rogue (This will only give 2 ASI, but will progress Sneak Attack by 2d6 more).
1.) I personally would rather have 1 ASI than 2 additional Sneak Attack die.
2.) I personally would rather have the Advantage in the first round + Auto-Crit on Surprise round than the extra bonus action BECAUSE i am getting Sharpshooter, and i want the -5 attack +10 Damage buffed by Adv+Crits.
TLDR;
1.) Go 5 Ranger to start.
2.) EITHER
--2a.) go 4 Rogue (assassin) then 3 Ranger (to utilize Sharpshooter better)
--2b.) go 7 Rogue (thief) to get 2d6 more sneak attack die and an extra Bonus Action to
Hide so you can Sneak Attack better/more often