This is how I would go about getting 1,000 people to sign up for autopay. You could have a $25 dollar option which would get the news letter and some initial item such as a shirt. That will take ground work but should be easy to sell. If they will commit to $50 you can hold a drawing for a nice prize each month. I am thinking around $500 dollar value which equates to 10% of your monthly intake. Limit winners to one time per year.
I would do one drawing for every 100 auto pay subscribers with the goal of getting at least 1,000 subscribers. 1,000 would yield 50k per month. In my example you would draw 10 prizes a month with a cost of 3k-5k. You can do guns, grills, season tickets etc The list goes on and on. I believe fans would jump all over that. Everyone likes to be a part of something. Fans showing their winnings on facebook will increase the exposure. That will be their chance to sell friends on the deal.
You can either give an entry to the drawing for every $50 dollars. A $100 monthly donation would yield 2 entries to the drawing. You could also do an end of year special for those at the $100 dollar rate such as a drawing for a cruise or trip to nationals etc. It would all depend on the numbers of donors. People not affiliated with the club can spread the word around football tailgating and give the contact info for signing up. I could get a handful of people myself. Thank you for giving us a line of communication.
You have some outstanding thoughts my friend! Keep grinding the gears!