Son's HS doesn't require you to "pay to play", however you are expected to raise funds to pay for your uniform. Of course you cant play without a uniform,
There are 3 "levels" of uniform funding... $250 will get you the base uniform, pants jersey & hat. For $500 you also get a pair of shoes and a couple of practice jersey's. At the $750 level you also get a team jacket and bag, a second hat and a name plate for your locker.
There are at least 10 fundraisers that all players are encouraged to participate in. They sell coupon books, Honey Baked Hams, business card ads in the program, signs for the wall. They host a golf tournament, a silent auction, Texas hold'em poker tournament, a home run derby and a summer camp. You can have a local business sponser your son, or as I prefer, just write them a check to meet your "fundraising goal"
Most of these fundraisers take place before tryouts. Last year we had 40 or more freshmen selling coupon books, signs, and hams for the Thanksgiving and Christmas holidays After tryouts only 15 of them had a spot on the freshman team roster.
I detest fundraisers where kids are banging on my door or hitting me up in front of the grocery store. Too many organizations do it. I feel like I'm always being hit on. Before I moved I knew all the kids or their families. I think I was giving more than $500 per year in addition to what I was covering my own kids. Whenever my kids had fundraisers I gave them the money and told them to leave people alone.
I hope your booster organization checked state laws before getting involved in gambling. I know of an organization that got nailed for illegal gambling over casino nights, football and March Madness pools. The team nearly got suspended for a season.