1. An affected user has been moved over new computer and outlook was setup from a fresh start (added account and redownloaded all mail items). Didn't fix anything.
2. The user who moved computers went from running Outlook 14.3.8 to 14.3.7 (and has had problems on both). I just saw there was a new update, 14.3.9 which is being installed now. All macs in the office are running OS X 10.9. There are other users on 14.3.8 who have not had problems.
3.The Exchange Web Service synchronization test passed (with ignore SSL warnings checked)