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Multiple shortlists would be great.
Better contract AI is definitely needed, for both teams and players. Both sides make some very questionable (and unrealistic) decisions. This is probably my biggest gripe with the game right now.
A better built-in logo creator would be nice as well. For fictional leagues it would be helpful to have the ability to create simple single-letter logos easily. I've never been a fan of the current game-generated logos and always used the ones I've created with photo editing software.
I'd also like to see more interaction/communication between GMs and players, similar to what EHM had. Being able to clearly communicate what the player's expected role is may help reduce the hits to player morale and the incessant whining from some players. There have been a number of occasions where I've wanted to tell one of my bench players "the only way you'll be in the starting lineup is if everyone else on the team and half the guys in the minors suddenly retired, so stop complaining and just be happy you're in the majors." Sadly OOTP does not currently give me the ability to do this.
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