Edit: I agree with AdamN, let the player decide from one month to two years, based on how they want to play, and the events of the game.
Also, the idea of acting through Leutenants is good, simply because it'll increase the survival rate of this game, and allow our accomplishments to be more permenant. However, I'd suggest we keep actual regulations low for two reasons:
1) Due to the nature of the game, tactical flexibility is essential for survival. I'm not gonna surrender somebody's mass murderer Avatar just because the Police show up and I don't want to play them. Ok, maybe I won't...
2) From my experience running the Association of Liberal Crime Squads, I conclude regulations probably stiffle and scare away players.
The player interaction dynamic is interesting. What do we think about one player who amasses $50,000 only to have the next burn the money on guns for suicide squads, leaving the LCS broke and hated? Would the first player be upset? Would the second player be praised for being humorous, or hated for being Conservative?
Do we have the maturity to say: It's just a game, and when I turn this save over, I realize the next player will probably intentionally lose, and I'm ok with that.
I like the idea, partially because it allows me to indulge my egotism, and partially because I never am able to finish a game of LCS. Oh, the game's fun too.