I used to play the [BLEEP] out of this game back in the day:

NFL Head Coach '09

Sure it's a game and is going to leave out a lot of the minutiae of real life and the cap is hard and not as massagable as it is in real life, but this game was great for NFL offseason and draft junkies.  You have position coaches and a GM you can hire and fire during the offseason.  Each has their own strengths and weaknesses on player development and evaluation.  Different GMs have different strengths evaluating specific position groups.  The combine results are posted for your review of measurables.  You bid on free agents.  When multiple school Pro Days occur on the same day, you have to choose which you're (your GM) is going to visit personally which unlocks additional evaluation about the prospects from that school.  You have several personal visits with prospects of your choosing which unlocks more information.  Ultimately if you scout a player well enough, you'll be able to see his "potential" score.  Guys with potential scores in the 90's are your league all stars and hall of famers generally.  Anyway, there's a lot more to it, but you have to navigate the draft with your big board with full info on some guys that you spent a lot of time on and partial info on others unless and until your GM's skills are good enough in later seasons, then you start unlocking a lot more prospects' "potential" scores and have a more accurate big board.  I don't play Madden, but I heard they just merged this game with Madden Franchise mode or whatever, but I heard the off-season stuff that this game focused on got watered down in the process.  I don't have a console system any longer, but I would probably buy one if they re-did this game with current rosters and updated graphics.

I played Front Office Football on the PC for a minute a few years back which is similar, but no where near as good.  Anyone with free time and into this sort of thing would get a lot out of the Head Coach game I think.  The Jags start in a tough spot that year with some bad contracts that need to be jettisoned and I used to generally fire my GM immediately and hope a good one is available to hire.  The free agent coaches and GMs vary year to year and aren't always the same play through to play through which keeps it interesting. Also, there are 4 distinct prospect tracks to be on and you are randomly put on one with a new start up and won't know which one it is until you get to your first draft and start seeing some prospects that are only on that particular track. Keeps it fresh on complete re-starts of the game.

---