I've created this discussion as a 'holding tank' for features and capabilities that the group would like to see within a league management module. Please feel free to add your thoughts and comments below.
If your feature request is related to a particular league module, I'd suggest also posting it in the issue queue for that specific module to ensure the module maintainer sees it. Once ULT is posted on drupal.org, I'll be using the issue cue to manage feature requests (though I'll take them here for now); and I know that Alun, the current maintainer of LeagueSite, is not currently a member of this group (though I've suggested he join).
That said, however, I still think it would be beneficial to the developers of any modules related to league management to have a one-stop-shopping list of features the group would like to see, so please contribute!