Couldn't Raoul also squeeze into Cade's space? You know, like you do when you start a grapple?
It's not gay when you're doing it to save a girl, is it?
Hmm... at least when he grabs R-J, they will technically be in combat, and so can't end their movement in the same space.
I don't see why this hinders your plan. Sequence of events:
Round 1 (this round):
1) Raoul casts fly on Xuuvosic.
2) Cade moves up out of the pit.
3) Raoul flies into the pit.
4) Cade moves back into the pit.
5) Xuuvosic grabs the pit and teleports (away, up, whatever)
Round 2:
1) Xuuvosic teleports up next to R-J.
2) Cade (who is just below the top of the pit, and so can still reach out of it) reaches over and grabs R-J, and then uses a move action to move down into the pit further.
3) Xuuvosic teleports them all away.
That's right, isn't it? If that's what you guys are doing, then I'll just move on with the game and resolve it like that.