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Stealth (dex based) check is for staying/going stealthy, Perception (wis based) check is used for detecting stealthed creatures.
Edit and "advantage with stealth checks" only counts for the former, as far as I know.
Rogues get sneak attack any time another ally is threatening the same target with a melee weapon (standing next to them). Maybe it was simply that? I don't think positioning does anything in this game in terms of flanking.
getting sneak attack from flanking and stuff is not a 5e thing. you're probably thinking pathfinder games
At least in this game you get sneak attacks from Threatened condition as well, despite it not giving an advantage on attacks against them. Not sure if it's a core or variant/home brew rule by Larian.
You don't need advantage on the attack roll if another enemy of the target is within 5 feet of it, that enemy isn't incapacitated, and you don't have disadvantage on the attack roll.
100% chance to hit does not sound right, no matter what, since 1 is always a miss. Unless I've been missing something. And by being threatened in melee range and having disadvantage at least the attack should not get any sneak attack damage bonus.