It's always bothered me that I can't simply come home with my phone and have it sync my Outlook calendar and contacts when it connects to the WiFi network.
It drives me nuts that I'm on the phone at my desk making an appointment with someone, open up Outlook's calendar, enter the appointment details then have to either type it manually into my phone or cradle the phone, run Desktop Manager and go through all of that crap.
Why no simple wireless sync? Enter it into one device, have it copied to the other automatically?