2. Unsure how laws would deal with this but if there options to create a money pl or even a money bracket where could pay a 5 or 10 dollar amount and have a payout of 80% back to the winners. You might get some interested if it was legal in some areas.
Welcome FBI and DOJ. Site would be shut down because of money laundering and/or illegal gambling.
1. Rename a player for one dollar - this would bring a couple hundred bucks per season
2. King of the Hill tourney - one dollar participation fee, winner gets supporter for one year, runner up for three months, number of participants capped @64, plays on sundays.