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Astarion, the Rogue-Assassin with a high Initiative, is one of the best ways to initiate combat for most of the game.
Use every advantage you can before striking. If all else fails, use an invisibility pot then attack.
As for sneak attack. You can use it whenever you like as a reaction, AS LONG as another party member is standing next to whoever you're attacking. Even if you're shooting them with a bow.
There are several other ways to trigger it. But the above is the most frequent.
Some spells also really help like fog cloud and darkness, and there are darkness arrows too. You can use all of these to lay down an aoe that you can hide in easily
So yes, it's possible, and satisfying when you pull it off.
All rogues can hide as a bonus action. Thief’s just get an extra bonus action.
That said heres how to stealth.
At lvl 1 your best bet is to click Shift+C to make all party crouch. Hold Shift to look where the lines of sight are and move around them. Do keep in mind that while not in combat you can use Shift+Space to go into turn based mode. This will allow for more precise movement all the while not risking panic button mashing.
On lvl 2 you can use a new ability allowing you to stealth using a bonus action. The blue abilities are for bonus action and yellow are for normal action. Its important because as a rogue if you are outside line of sight and in combat you can just disappear. But keep in mind the enemy knows your last position and will go there and use See Invisibility action to look for you which will force you to roll for Stealth.
About Suprise Attacks. They dont need you to be in stealth to work. They just need advantage which means you can go between enemies, have a cleric cast guiding bolt on your target and then you can Suprise Attack them.
Shift look is important. Other than line of sight it will also give you info for how well the are is lit. You have either dark, shaded or well lit. All of those will provide either no bonus or some bonuses to your hiding skill.
On lvl 3 you will be able to choose a subclass. From this point i cannot give more advice because it depends on the build and there are million of those. That being said, other than tips above i have some general tips for your rogue.
Dont dismiss potion making. It can be a very usefull mechanic to create potions and use them. Coat your weapon either in some oils or in fire (always carry a candle for that). But other than coating use a potion of invisibility and other stuff that grant you that like equipment. You being a rogue doesnt mean you are invisible by default.
Use distractions. A well placed illusion can grant you a turn or two in turn based where you can slip past enemies to a better position. Use bards to play music and gather crowds. Use your friends in coop to start a conversation and make NPCs look in other directions. Its super usefull if you get the hang of it.
Use spells. Darkness and a race with Darkvision is golden. Pass Without Trace with True Invisibility Potion will allow for infinite invisibility stabbing. Teleportation spells can allow you to not risk even trying to sneak past someone.
Play what you want but i recommend doing a custom character build. It allows for two chosen proficiencies from the list instead of having set ones like origin characters.
Remember about proficiencies because they will change how you play. Rogues have double proficiencies. Dont dip them in random skills. Max your stealth capabilities if you wanna sneak. If something boosts your sneaking then take it and use it. By act 3 you will have too much supplies so dont hoard stuff, use it.
Use social stealth. Remember that you dont need to sneak if you can use Disguise Self and lie your way into enemy ranks. Goblins will bow to drows, tieflings are considered evil, races will be more willing to cooperate if you are the same race.
No one shoting. Sorry. If you dont max yourself into assassin and do a very specific build for it you will not be able to oneshot people. However nothing stands in your way to change classes of other companions at Withers and just have a assassins guild as your party.
With all that being said remember there are mods to change the game if you dont like something. There are easier difficulties. There is a custom difficulty. You can customize the game to have fun.
Also, you only need advantage on the attack roll, or the target threatened by an ally, to get Shneak Attac, you don't have to be hiding.
True, you'll get the Sneak Attack dmg if the enemy is threatened, but you won't attack with Advantage so you'll miss more often. It's preferable to hide first as your Bonus Action.
Yeah, big surprise, ducking behind a lamp post while someone's looking at you doesn't fool them. XD