Correct me if I'm wrong, but I believe free agents automatically choose the most lucrative offer. Would you consider adding some more logic behind this so that certain players (e.g. younger first-time free agents) are more likely to pick the highest-paying contract, while others (e.g. older ring-less veterans) are more likely to select a contender even at a lower contract? Potential playing time could also factor into the decision.

It doesn't have to be so black and white. There can be a probability that a younger player chooses a contender while a veteran chooses the best offer; however, something like this would make free agency more interesting than simply out-bidding everyone else.

I probably won't do the contender logic just because that would help the good teams over the bad, but I do intend to implement player attitudes toward owners in the next engine (see my response to your comment in the other thread) - and have considered giving owners a reputation score within the league that might cause players to sign/shy away from them. Haven't decided on that last one yet.

Player personalities might help with this.

Greed, playing time, location, system, loyalty, player connections, playing for a winner etc...
These attributes could also affect their play on the field to a certain "hidden" degree.

I do think those are all great ideas - I had thought of most of them except system, that's really a great thought.