We are going into our fifth season as an amateur league. Last year we charged 25 dollars which covered a league dyed disc and a graphic T-Shirt with our logo on it. The few cents left over was invested into traveling trophies that can be passed down from year to year. That was the mandatory fee. Notice no prizes outside of the three trophies were built into that fee. It really takes people who want to have fun to commit to 25 dollars where there is no monetary pay out. Currently we have 15 to 17 people.
We do run voluntary things like Ace Pools, Bag Tags, and CTP Pools. The Ace Pool is straight forward. 1 dollar per round. No one hits it, the money carries over to the next league event. However, you must contribute in that event in order to win it that day. If you do not invest that day and hit an ace, too bad, even if you had invested in the past. However, if it is one of those bomber courses where only a few of us can reach the baskets, the ace pool is not active unless at least five people contribute. We also run CTPs. If the Ace Pool is not active, people can contribute 1 dollar per round but that is immediately paid out at the end of the event; not touching the ace pool. Regardless, we kept track of all the CTPs throughout the whole year. Every event has at least 2 CTPs regardless if we are playing an Ace or CTP Pool. The top three players with the most CTPs split up whatever money was left in the Ace Pool at the end of the year. Year 3 had an ace in the second to last event, carrying no money over, but Year 4 no one hit an ace and we split 90 dollars three ways (50/25/15).
We also ran bag tags at 5 dollars a pop. For production sake we used high quality poker chips, burnt the numbers into the plastic, drilled a hole through the chip (it was fun discovering that poker chips have metal in the middle), and attached a key ring. The whole production cost 1 dollar per chip, leaving 4 dollars per tag for prizes to be split amongst the three lowest numbers present at the year end event. (35/15/10)
This kind of money guarantees you cannot run it at school. As a teacher I am instructed in what constitutes as gambling, and as silly as it may sound, since money is exchanging hands it is a form of gambling. If you did it strictly for fun but have a club status, no money involved, you should be able to get it approved as long as a licensed teacher is involved and or a grownup who passed a criminal background check. If you want to collect fees just to strictly cover expenses, you definitely should get the school board involved. Since it would not cost the school any money, I do not see a reason for them to turn it down. You might even be able to push Innova's EDGE program (which will cost the school money but under the Presidential Initiative to promote healthy lifestyles your school might find some federal funding for it).
We only meet once a month as a whole league, making sure it is a different course every time. This gives people an opportunity to go out and play a course they rarely do, and likely several times as they get some practice. However, we schedule three individual head-to-head matches for each player every month. They can be played any where and at any time the two players can schedule it as long as they are completed before the next league event. Since most of us are working age, some with kids, this type of scheduling works out great.
One thing our league does every year is a road trip encompassing three days in late August. Year 1 and 2 we played all the courses in and around St. Cloud (MN). Year 3 and 4 we camped at Highbridge, WI. Next year we are thinking of hitting the best courses around Des Moines, IA.
Lastly, Year 5 we are thinking of upping the entrance fee to 30 dollars. We are also considering hosting a Discraft Ace Race. The extra fee in the money is going to be a for a league t-shirt and an admission into our Ace Race. We are technically losing the league dyed disc, but will be gaining the two prototypes as well as the rest of the player's package.
Hopefully this gave you several ideas.