This sounds super time intensive over an extended period of time tbh, but kudos to whichever of your friends is making that work! If we had to do that in advance (lots of rebuys etc), I don't think it would work.Welp, I play fairly regularly on a site where the guy maintains accounts, so yes, everybody plays in advance.
I’ve played online tournaments with four other groups this year, and with each one, people were expected to pay before, or in the early stages of the tournament.
So I, for one, have never played online where the cash is all settled up later.