I will still wait a bit more on the poll to make a firm conclusion (id like at least 4 votes in total), however i want to do a raffle this month as soon as possible, so i will use the new proposed system if you guys wont mind and that means that i will do one for Wolfe

Math:  gross / wins  + (months_without_win - 1 + 3 - Tier)^ 1.3 * 5 * (gross/tier_price/payments)
Wolfe score next month assuming they pay:  236.7 -> 50

And the month after if they dont win: 64.8,
which is a small increase, but it will increase exponentially becouse they pay and not win, plus the month count multiplies score exponentially

As you can see, this way everyone should technically get rewards based on support amount. If everyone supports equally, likely i would give rewards to everyone in a sequence