I don't think everyone is going to want to pay $5 for each match for each round, are we planning on the winners transferring back the funds?

FWIW, I've played this structure with a few members of this forum the last few nights and there is a little play involved, but certainly not as much as there would be 100bb deep. I mean, I feel the better player will win in the long run if we do best of 5.