Back in the day.... I always considered the group organizer to be the key. I offered a free pass for every 15 players (#16,#32,#48, etc ) and the group organizer could convert it into free paint or cash. It worked out to $3 per player (about 10%) the organizer could pocket or use to lower everyone's entry fee. The group organizer would collect the deposit I asked for and collect the remainder on game day making my job that much easier.
For gear owners a reward system seemed to work much better than a membership. Paying up front for a discount to be received later seemed a little much to me so I gave them a reward for loyalty. Every 5th day free, bring a buddy once free, entry into events discounted, etc. Loyalty soon became a non-issue. Gear owners came for the experience, not the price, but I'm sure it helped keep them.
One thing I never gave discounts on was paint. One low price fits all, gear owners could bring their own paint but mine was priced low enough and was always fresh so they didn't.