I’ve found quite difficult to use a sneaky character mostly because it’s quite impossible for me to avoid close combat.
What are the best strategies to ‘one-shot’ an enemy or to deal with a crowd?
Use dagger with a bow secondary, because they have x5 and x3 backstab damage multipliers when sneaking. (assign shortcuts for both sets)
Get some invisibility rings and robes (or enchant them) (but don’t go over 90% invisibility), if your a low level get invisibility potions, this will allow you to avoid combat and sneak through dungeons.
Get night eye.
By invisibility I obviously mean chameleon invisibility.
If you get in trouble you can always drink an invisibility potion and escape.
I passed all of the guild quests and the main quest as a stealth character with a dagger.
I ended up getting some chameleon rings and robes which made me 100% invisible
Here you can see me in a restricted area, notice how the guards ignore me.
(the sword is white because of some bugged weapon skin)
the game lost it’s charm for me but it’s certainly easier to play someone 100% sneaky
Other than that I suggest you get some chameleon rings and achieve around 90% invisibility which is pretty fun to play at and is significantly easier to deal with crowd’s which also allows you to use the dagger stealth kill modifier (x5) which is better than the arrow one (x3). (, the difficulty level was close to max, and the arrows were useless, so to experience one shot kills you could always reduce the difficulty)
night eye beats any torch or anything that is visible to others, although just setting the in-game brightness is very close to night eye so use that if your having trouble seeing in the dark.
one example is when I was doing a assassination mission on the countess of anvil, the game felt like a real stealth game then.
Good luck! and remember, challenge is what keeps the game fun, challenge and leveling up (and some stories)
p.s. Thieves Guild missions are the best.