ipod/Outlook sync problem solved -- may work for iPhone
Here's the short version: Couldn't sync Outlook Calendar to ipod. (Contacts, music, etc., synced okay.) This fixed it:
-Back up the Outlook.pst file: Open Outlook, click "File"; "Import and Export"; "Export to a File"; "Personal Folder File (.pst)"; select "Personal Folders" and click in box for "Include all subfolders"; choose where to save the exported file, and click finish. Close Outlook
- Open Outlook, open Calendar; choose "View"; "Arrange By"; "Current View"; "By Category". Click on "Start" column heading to sort by earliest date; select everything up to 2007; and hit delete. close outlook.
- Connect ipod; allow iTunes (make sure its the latest version.) to open Outlook and sync. It worked. ipod now has all calendar events from 2007 on.
My wife and I have two unpoened, in the box, (!) iPhones sitting on my desk. I'm a mac user. She has a WinXP Media Center with all updates, running outlook 2003. She also has a older ipod - 20Gb with the click wheel/B&W screen. She has used it extensively but has never been able to sync her outlook calendar. iTunes (7.3.1) appears to be syncing - the hard drive chugs away for a few minutes. Music, Audio Books, and Contacts come through just fine but no calendar events. Since Outlook is hardwired into her very existence, we agreed that if we couldn't get the ipod to sync the outlook calendar, we would return the iPhones until the sync problem other iPhone users were experiencing was resolved.
Since I have a Macbook that is begging to meet up with the new iPhone...I have been motivated to solve her ipod sync problem!
I tried everything that has been suggested here and on the Apple website to no avail - no calendar events on the ipod. The fixes didn't seem to be the problem... hmmm maybe something to do with the size of her outlook calendar.
Well, she had calendar events dating back to Dec. of 1917! Many, many friend's birthdays entered as recurring events and a myriad of other stuff. I exported her outlook.pst file to the desktop of her PC as a back-up then I opened her outlook calendar and set the view to "Category View". Then, I selected all events before 2007 and deleted them. Closed Outlook, connected the ipod to her PC and iTunes opened itself and began to sync. Outlook opened by itself (iTunes seems to do this as a part of the sync.) The sync took far less time than before and..... THE CALENDAR SYNCED!
I didn't check every calendar event on the ipod after the successful sync. I can't say if the sheer number of calendar events was the culprit or whether the very early year dates confounded the iTunes. Hope this may help someone.