I've never hosted a cashless game live. I've been hosting on a Mavens site since the pandemic, though, and that's of course cashless.
I start everyone with the same amount of credit, let the night play out, and use the resulting balances to make a payment structure that gets everyone back to zero. Then I reset all balances to the default and send out an email that looks like this, only to the players involved:
View attachment 1045325
If there's anything that requires a decision (e.g., which way to round 0.50 to make it all zero out), I flip a coin or draw a card or whatever. Same way I decide to who has to make more payments than the others, like Jackie and Bobby here, if it's necessary to do so.
Honestly, it's not bad. Once I got a good method down, I could knock this out pretty quickly. Importantly, it keeps my digital hands off the money. No one pays me and I pay no one, and I like it that way. (I've been taking a break from the game, so I'm not even involved as a player anymore.)
All this said, I consider e-payments a stopgap measure for a very specific problem. If I'm playing a live game, I'm cash in, cash out all day. A few other users have already articulated my concerns quite well.
I'm very interested to see how the new IRS rules with regard to reporting for peer-to-peer payments will play out in the coming months. I hear a lot of talk about people using F&F payments instead of business, but I wonder how much that will matter.
Be a hell of a thing to have to tell the IRS that all that money coming in and out isn't income, but you acting as the bank for an unlicensed gambling event every Wednesday for the past year.