how is he setting up a new account? The only reason i ask, is that I assume this is your only way to confirm that no other money has been deposited in the account (which i guess means that you would have access to this account also so that you can confirm the deposits).

Anyway, I think this is a very interesting wager and wish you both good luck.

If I understand steps right, I think you are on the better end of the wager. He basically gets 5 tries at making something happens (inside of those 5 tries he can have numerous retrys by way of freerolling, but essentially he is not going to receive any money for placing in top spots, since it only gains him access to the next step, so his $30 will never increase). 5 tries only, hmmmm... I hope he's good, otherwise very bad wager for him.