So the initial rule for keepers is you get 1 less if you win the Presidents Trophy or the playoffs. I'm thinking maybe the Prez Trophy part should be scrapped, so it's not a punishment to win that, and therefore finishing 2nd would be best.
Rule was copied from my other league where there's a cash prize attached to winning Prez trophy, so it made sense. If everyone is fine with that going forward, I'll edit the OP.