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I have chosen not to ever commish any ootp leagues, but I used to administrate large online text games (1500+ users) in the mid-late 90s and we learned a few things about problem players there....
1) Sometimes problem players just made a mistake, or erred on the side of bad judgement. Not necessarily a bad person or a constant thorn in the side.
2) Sometimes players will have purposely and with intent did something wrong, but with time away realize their actions were inappropriate and are more than willing to mend their ways if allowed back in.
3) Sometimes players will take as much rope as you give them, and always hang themselves. You give them 10 chances, they will constantly see how far they can push you, or push the rules.
What we used to do was anytime someone did a serious rule infraction we would suspend their account and put them in a form of a "penalty box". If/when they contacted us, we would talk over their behavior/infraction and if they truly seemed sorry and interested in repaying the game for the wrong they did we would usually re-instate them with the final warning rule. Any infraction they made (even small ones), and they would be permanently gone. No second chances any more. We would make it clear to them and never bend on that. (There were several who tried us).
THe main reasons for second chances in those cases is that you never know someone's identity online.. you don't know if a new player is a legitimate new player, or just some old player who created a new account. It was easier to keep potential problems in front of us rather than guessing at who they were.
And there were many times where problem players became good contributers to the community and were not problems ever again...
Anyhows, just my experience whatever that is worth (I think it + $1.50 will buy you a coke these days.)
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