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Creative thinking I like
Whether the COMMISH likes it is of course what matters.
I like the idea of rewarding success in some way, but there would need to be something to not discourage someone from picking up a hopeless franchise and trying to rebuild it.
Perhaps if you made it for the owners whose teams as a whole improved the most from the previous season? That would encourage you not only to try hard with a top team but also to not neglect a poor team. Every win would count.
I'm opposed to a penalty - I think you are more likely to get a desired result from the carrot than the stick. In addition, some of us are just not as good (or lucky depending on your view) as others. Your penalty seems to imply if you aren't winning it is because you aren't trying. If one person has a .560 winning percent, someone else has to have a .440. That doesn't mean he wasn't trying.
I also don't think all rewards need to be monetary, just a little recognition might be useful. How many of us have tried to get high score on a the video arcade game just to get our initials up for the next player to see? (and spent a lot of quarters doing it?).
A discount or free LL or some such for getting someone to join is a good idea though and that should be worth a monetary reward.
How about a free LL for all managers who make it to the league championship? That should be a competitive LL. Or for the 20 managers whose teams improved the most from the previous year? Contests within our baseball contests could add some excitement - there could be a running status posted weekly on the forum for instance.
I'm rambling and getting off point. Bottom line, I generally agree.