Horrible idea. Would you trust the Sim AI to set your budget, re-sign free agents, sign (or fail to sign) other free agents, exercise options, and arbitrate? I doubt it. Then why would somebody want to join a league where the Sim AI has done just that to the team they're taking over...and started the team out on a 3-25 record to boot? How about agreeing to trade proposals? You don't think the human owners might go out of their way to fleece the dumb sim teams of their best prospects before someone with a brain takes over?
You would have about 20 owners in the world from rollover cornering the market on all the good free agents and taking all the talent from the sim teams, completely stacking the deck against the incoming owners.
Just do what shobob said...find a better world where the rollover isn't as long. Trust me, they exist.