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Just a random thought.
The alleged problem is bad GMs who don't know what they're doing, mess up their team and so quit leaving the 'good' GMs in a lurch while those who took advantage of the bad GM get ahead.
First....a monetary prize is not going to solve that. It is going to make it worse. Now the 'evil' GMs have incentive to take advantage of the newbies.
Second, charging a fee isn't going to make the bad GMs better. It MIGHT scare them off trying....which is bad for the game as a whole.
What I'd suggest is two fold:
First, in online sim leagues I've seen rules are the most important tool I've seen to ensure fair play. Use a salary cap. Maybe share revenue. Don't allow draft trades, and maybe the commissioner should be able to veto trades "not in the best interest of the league" if he's not playing. (If he is then a three-man council, like the early days of MLB, might be a useful idea.)
Second, the only way these bad GMs are going to get competent is if you let them play....and maybe let them fall on their face once or twice. Real life GMs get suckered too. Teams can recover from even catastrophic trades, and the 'evil' GMs will eventually develop a reputation for untrustworthiness. Especially if the league has an active forum.
As for the 'bad' GMs....train them. Part of a responsible commissioner's job is to maintain the health of the league, and sometimes that may mean mailing them and saying "Uhm...are you sure you want to do that?" If there's a small body of trusted, experienced GMs maybe one who's not a competitor (different league, whatever) gets assigned as a coach to answer questions and offer advice.
Paying for a league is valid for dealing with administrative expenses and time spent keeping the league functional. I have no problem with that. As a tool to encourage fair gaming it will backfire however, and as a tool to encourage the 'right' kind of GM...sends the wrong message to new players.
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