I think the show could use a lot more wholesome segments, so with the knowledge of the behind-the-scenes cast dynamics I would choose people who would be most likely to want to do things to make each other's lives better.
I loved the episode of Game Changers where the cast just tried to make Jess happy. An episode where they all do improv for free so they can give each other $1000 in cash at the end of each segment would be in a similar vein.
While I agree, the show is very much still finding it's legs, but I do think the newest episode (episode 3 for those from the future) was the best episode so far.
For example, I did not like Sam's segment, but I loved Katie's. Which I don't quite think is Sam's fault in the same way as Tao's (because he basically rigged it for himself).
Though to awnser my own question, I'd probably do the World's Beyond Number crew, Brennan, Erika, Lou, and Aabria.
Tao's was absurd. The only excuse I can think of is that he thought it would be funny to win his own challenge and it didn't quite land. Otherwise he's not playing within the spirit of the game