Spent some time last night trying to work out the best way to calculate a few of the steps of my play. If a player comes to help on defense and leaves his man, the ballhandler has to decide to either attack himself, or look for the open man. To make the decision, I use the court location of the offensive player as well as his attributes to determine whether it's a good option to pass to that player.
To use this pick and roll play as an example, if the PG comes off the screen and finds himself open, the defenders of the 2 and 4 man have to decide whether to leave their man to hedge the ballhandler. This decision is based on strategy - there is a hedge setting for each player on the court - vs defensive awareness to see if the player correctly acts on that strategy. If either defender hedges, a check is made on the 3pt ability of the 2 man on offense, and the 4 mans inside ability from the low post to determine the "best" decision - then the players offensive awareness rating is used to determine if he makes the best decision.
I currently have the sim functioning as above, but I'm trying to add some more complexity to it. I'd like the defender to take into account the guy he is defending when deciding to hedge - for example, you probably wouldn't leave Ray Allen to pickup the ballhandler in this situation. I'd also like the ballhandler's decision to not be so simple, because maybe the guy in the corner is a good shooter, but the PG might still be better served using his own abilities to attack.
Again, the advantage to making this as complex as possible is that, once I'm happy with it, I can reuse it every posession that requires similar decisions. It's just getting it right that first time that has me pulling my hair out.