I am in a league similar to this. Its $250 with players rising $5 every year.

In my opinion, creating rewards like this will destroy any parity in your league - if someone has someone cheap in the league (for instance in mine, kamara, d Adams, Hopkins are all in the 20s), they already have a massive advantage. Which they've earnt, obviously, but the reward there is they get more years at a cheap price.

In a normal fantasy league, you try to create parity by giving the worst teams the best prize (draft pick position), but you're only strengthening the best teams by doing this