While this probably isn’t news to many, I have almost come to the conclusion that syncing a handheld with the desktop is dead. The only exception is media as OTA (over the air) sync is far too slow (currently) to handle large photos, music, and movie (for the most part). It has taken me awhile to come to this conclusion as I spent many years working on desktop sync software. In the last few weeks, we installed Zimbra at work and are moving people towards syncing their handhelds (Windows Mobile, BlackBerry, iPhone, and Palm OS devices) over the air (primarily cellular). In these cases, the desktop just becomes another sync client and not the master; the server handles the synchronization.
My life seems much simpler now that I don’t have to deal with desktop sync; no more desktop configuration, physical connection issues, and various conduits.