I have to say this looks rather ill-planned. There are so many problems with this system that I don't know where to begin.
Amounts are approximated sloppily, and you're told up front that some people might not get paid and some people might not have to pay. The middleman pays out first, trusting everyone to send in the owed five-spot later by their own means. Can you say "bankruptcy," kids? A vast number of members won't bring their wooden-nickel tally past $4.95. The well will run dry fast, even assuming all participants are honest, and they won't be. What an easy scam! A whole bunch of friends would each donate four dollars of other people's money to one agreed-upon recipient and split the take.