I’ve never had an iTunes/iPod sync issue… Until this evening. I ran into problems related to the iPod touch January Upgrade released today and announced on Macworld 2008 this morning. You can read the gory details in the blog item I wrote for the O’Reilly Mac Center.
I discovered one item in favor of the Windows Mobile platform after performing the iPod touch upgrade. The iPod touch mail client (and presumably the iPhone’s mail client) does not support SSL encryption for IMAP4/SMTP mail configurations. CORRECTION: The SSL option is in the Advanced tab.