Rather late, but I finally got around to trying this out. Overall, I like the concept, though I ran into some issues with the UI - because I've got a high resolution display, I can actually just keep all the windows open. Unfortunately, they don't always update unless I close and re-open them (the contract list was especially bad about this).
The main things I felt lacking during my playthrough where the amount of content and complexity, but that may just have been me not getting far enough into the game. In particular with the complexity, I'd want to see more ways to fail or for things to go wrong - I think the half sports team manager idea you mention in your comment would help with this.
Also, a minor thing, but being able to pause or unpause the game with the spacebar would be really nice. I usually play simulation/management games at max speed and just pause when I need to do stuff.