theobscure,
I think this game should be right up your alley, given what you've shared thus far.
[broken record]Enjoy v.5 for free and get yourself immersed. v.6 is much better and there's no doubt 2006 will be even better[/broken record]
Also, if you want to see the scope of what kind of fictional leagues can be created and enjoyed, you might want to check out some online leagues as well.
I'd recommend browsing around in the alternate realities of the following:
The Kabalian Baseball Leagues
Corporate League Baseball
The Western Hemisphere Baseball League