OK Allan and Dahveed. So tell me if you think this will work.
1) I go to iTunes and open a new family ID
2) I log in that account in iTunes on one of the computers after authorizing the computer to use that new ID
3) I plug in the iDevices and transfer purchases from the file menu without synching.
4) I log into the family account on the other computer's iTunes and tell it to search for app and music purchased from Apple but not already on the machine and it will update because all IDs are authorized.
5) I put up with the hassle of trying to remember which account was used to purchase which app and occasionally log into the old IDs to update those apps. Obviously, free apps should be redownloaded with the family ID.
6) Overtime the apps from the family ID will take over and it will become less of a hassle.
Is that how it works? Am I missing anything before I start this venture?