What is the archetypical way to use a hide-then-strike-with-advantage-and-sneak-attack-bonus-strategy?
I don't think there is an archetype because sneak attack doesn't work the same in all editions. I'd start from the RAW and check what happens in 5e:
- Sneak Attack works when you have advantage on attack rolls, it doesn't matter why you have advantage (it also works when the target is busy in melee with another enemy, but let's focus on the first case only)
- if you are hidden, you have advantage on attack rolls, therefore Sneak Attack works
- however, getting out of the hidden position to make a melee attack OR attacking (ranged) from the hidden position, automatically "reveals your position"
- nothing says if you can just make another Stealth check immediately and go back to hidden, and/or if you are required to actually change position
I think I'd adjudicate case-by-case the latter point.
I am an assassin, and I use my turn to walk into the shadows (dim light) and hide. There are four enemies in the room, one of which has low-light vision. I roll for Dex(Stealth). DM rolls for the three enemies that is concerned with the dim light. (I presume that from the low-light vision enemy I cannot hide?). It turns out I beat the perception check of two of the enemies but not the third. So I am now hidden from two enemies.
I assume here you mean you have the Stealthy feat i.e. you can "hide when lightly obscured". Dim light makes you lightly obscured. Low-light vision allows to see in dim light as well as if it was bright light.
The ambiguity is, which one is stronger, Stealthy or Low-light vision?
Does Stealthy turns dim light into darkness? No, you can hide in it as if it was darkness but it's still dim light, so someone with low-light vision can still see clearly in it, so you cannot hide!
OTOH
Does Low-light vision turns dim light into bright light? No, you can see in it as if it was bright light but it's still dim light, so someone with Stealthy can still hide in it, so you cannot see it!
I'd be more inclined to rule in favor of low-light vision, but I wish the RAW was more clear.
a- Can I be hidden from some enemies and not some?
b- Could the enemies that sees me alert the others of the danger?
c- Can I sneak out over the well-lit floor to sneak attack someone out there?
d- If so, is it a Stealth vs. Perception situation? Anyone with advantage/disadvantage?
a- yes, it's a skill contest vs each, so why not?
b- no, or actually yes of course, but not as to negate the penalty: they can tell you someone's hidden over there, but if you didn't see it with your perception check, you still don't see it
c- see above, I'd say yes if you are fast enough (i.e. if you start your turn hidden and attack in this turn)
d- yes, technically the skill contest is when you start hiding rather than when you attack, no special adv/disadv in this case
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