Possible partial solution to 3g syncing problem iPhone

After numerous attempts to restore from a backup, I gave up and decided to restore as a new phone. I ended up having to restore to a backup from august 09. Even after I restored the phone, i couldnt load any music, podcasts or photos onto the phone. I would get the following:

But itunes could find the file when I did a Show in finder and could play the file in the computer.
I consolidated the library, didnt help.
I removed the songs from the library and then re-imported them, didnt help.
In the end, I downloaded a podcast to the phone from itunes directly, and that solved the problem. Almost like the phone didnt know it could accept media until it came from Apple directly.
Hope this helps a little bit.
Dual 2.3 PPc G5, Probook duo 2.4 Mac OS X (10.5.8)