Hi Collin
Well the phone has been backed up a number of times when I've plugged it in for syncing, and I've downloaded a few apps, but only through the phone, not via iTunes on the iMac. You've answered another question of mine in the OSX section about ports, here's what the error report says:
Open the proper ports and allow access to Apple servers
During the update and restore process, iTunes needs to contact Apple. Ensure that your computer has the following ports open and can access these servers:
* Port 80
* Port 443
* phobos.apple.com, albert.apple.com, gs.apple.com
If you see "Error 9807", you must open access to the following VeriSign servers:
* evintl-ocsp.verisign.com
* evsecure-ocsp.verisign.com