Mystery solved! I had issues with Pocketmac not opening (bouncing icon). I have uninstalled and reinstalled so many times that it was not funny. Determined to figure it out, I stubbled across the Blackberry Media Software for Mac, installed it in hopes that maybe it would fix something. The software installed and it indicated that It was not compatible with my iTunes and that I need the latest version. I checked and I did have the latest 8.1, so then I assumed the Pocketmac issue was attributed to an issue with my iTunes and in fact it was!
How to fix:
1) Back up (copy) your iTunes music and files to your desktop.
2) Completely uninstall iTunes with these instructions
[Only registered and activated users can see links. Click Here To Register...], complete the entire instructions
3) Reinstall iTunes
4) Open iTunes, accept the agreement and go through the setup. Close iTunes and copy your files back in your Music ITunes folder.
5) Open Pocketmac and enjoy syncing with Entourage