OP, after posting the sitter will have 50 chips, so raising is correct, because he is sitting and will fold. Villain2 will be left with 600 chips for the next HU hand. I'll take a 13 to 1 advantage into HU any day.
in the revised hand, it looks clear to me that villain2 is ICM'ing it and wants the sitter gone. Again, sitter will have 50 chips left, and Hero will either end up with sitters chips or villain 2 will in the next hand.
Hero wants those chips.
So in both cases, raise, get the free chips, and move on.
I think perhaps this problem should back up 4 or 5 hands when it was not nearly as clear that villain1 would essentially blind out. Assuming standard bubble play, it is likely that V2 has been trying to out sit V1 to be sure of making the money. So showing pressure on V2 several hands before this was where ,IMHO, the real action was.
I might be inclined to fold if V1 was actually there, because V1 could add some actual challenge to V2. But still, in both cases I'm inclined to push the tourney along to its end.