I used to run lottery events with my old crew. It would work like this:
Tickets cost 100 PoE. After a nice prize is built up, I use a quasi-random number generator to select a random ticket, announce its owner, and give the winner 60% of the PoE and a nice little prize on top. The remainder goes to the flag. You can repeat it over and over again for a continual stream of funds, and it works really well as a way to get pirates without a ton of money to help the flag out.
I can implement this rather painlessly in my crew, and probably will shortly. Just a heads up in case ye all want to do the same in your crews.
-C