Maybe I'm not being clear. We're using terms year and season interchangeably. Let me try again. Here's what I envision. (this is without accounting for Cup winnings and payouts are just for example).
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Let's use Team 7 as an example to start. They paid $75 for the year Spring and Fall. They got relegated in the Spring by finished bottom 2 in League 1. But then they won League 2 in the fall and promoted back to League 1. Next year they would pay $75 again for the year (spring and fall) if they so choose.
How about Team 8. They paid $75 to be in League 1, but finished dead last in Spring. Then they still didn't do well and finished 7th in League 2 in Fall. Next year they have to start in League 2 for $50 for both Spring and Fall fee.
Team 9. They paid $50 to enter league 2. Won that in the Spring. Earned auto promotion to League 1 for Fall. Finished 2nd in League 1 and therefore a larger winnings then they would have as 2nd place in League 2. Next year they would have to pay $75 to start in League 1. If they don't want to, they can move back into League 2 for next year at $50 and we give Team 11 the opportunity to start in League 1 for $75.
This make more sense?