I require someone to hold the cash at the time. Perhaps Alan, if he's willing to take on the responsibility. I don't know you and I'm not willing to take a chance on getting free-rolled.
I don't know what you mean by getting free-rolled, but fine by me if Alan holds the money.
I would suggest that we pay immediately after each decision.
That's how I play golf with people I don't trust to pay after the round, we pay up after each hole.