Does OOTP handle the pre free-agent market well?
Any contract structure that's in actual baseball can be created in the game.
For example, you could go all Dave Dombrowski and DESPITE Cabrera having 3 years left on his contract ... and DESPITE him being in his 30s .... you could offer him a 10 year contract extension that would make him the highest paid player in baseball history...
In OOTP - you might be forced to make such an extreme decision if a player's perception is that other teams have greater salary cap to work within and they could stand to get paid more elsewhere.
The financials portion of the game is pretty mindblowing. I haven't experienced all of what's out there, but it's worth a quick lurk over at the OOTP forums to see how people's franchises are going because the diversity of situations and outcomes are seriously interesting to read about and watch.