So X will teleport up with the pit, Cade will jump out and grab Ris-Janna, and they'll all start falling. X will then teleport himself and the pit back to the ground. Raoul will then use Tactical Teleportation to stop Cade's and R-J's fall and have them plop into the pit (or onto the ground or whatever. Don't forget that the pit is 50 feet deep... although at least half of that is currently filled with burned goblin bodies and scaffolding...). Then next round, X will teleport you all away. Sound right?
The only problem I see is that X can't fly, and so there won't really be much time for Cade to jump out of the pit before X (and the pit) starts falling away from R-J. I guess if they start above her it should work, though. It would all work better if X had a Fly spell, though. He could then hover like 200 feet above the tree-dude and R-J, and Cade could skydive from there down to grab her. Although... I should probably enforce falling damage on you guys for colliding with people in mid-air.
And a clarification... you don't only fall on your turn. Everyone's turns technically happen at the same time (a round is only 6 seconds long, not 6 seconds times the number of combatants). Things do happen in an order, though. So you can time things to work out as above via readied actions and the like. So yeah, I think this will work. You can talk about it in-character and then you and X can post your actions to pull it off. Cade will need to make a touch attack to grab Ris-Janna as he goes by, also. Since she's unconscious, she can't resist his grapple attempt. He'll have to use his move action to jump out of the pit, so he'll only get one try, though.
Also, in the future if you guys are falling past someone I'm only going to allow one melee attack as you pass, contrary to what I allowed X to do earlier. That's the way it works if you ride past someone while mounted, so we'll stick with that. If you're making ranged attacks, you can make them all (also as it works while mounted).