Windows 7 (64 bit) iTunes 9.2 Outlook 2010 Sync Issues

I’ve noticed bunch of conversations here about issues with the new version of iTunes NOT syncing with outlook contacts / calendars but none of them seem to be resolved. I also have lost my calendar sync since I installed the new iTunes. I have un-installed / re-installed iTunes, tried creating a new PST file, created a new mail account, tried pretty much everything I can think of and nothing works. I have wasted more than 23 hours of my time playing with trying to fix this and I am getting pretty fed up. My question is has ANYBODY actually made it work. I fear we may be wasting our time meaning that there is a bug that no one at Apple cares to acknowledge. Thoughts?

Hello,
I've been searching through the forum, but did not find someone having a real solution in my situation having the problem as described above. I defintly CANNOT delete all my recurrent appointments! I have about 10.000 elements in my Outlook calender, because I'm really using it for planning my whole business day. Isn't there another solution?
I was syncing my iPad-calender with MS Outlook (2003 SP3) successful during the last days, but "suddenly" (I think, it was after the iTunes Update) the syncing process was silently stopped as beeing successfull, and no appointments were synced anymore.
I already followed the rules to resetting the syncdata history of iTunes and also forced to overwrite the iPads calender, but it still remains as before.
Then I decided to delete the calender by stopping the calender syncing, I mean, I deactivated the hook and then iTunes asked, if I will delete all the data on the iPad, where I then agreed to, as you also describe. Then the calender was successfully emptied, but activating it again after syncing, the OLD state is synced back to the iPad and not my currently modified scheduled appointments from Outlook. This is a miracle, because these are old/deleted data!!! It seems the iPad is just doing a "undo".
I already tried the "Help -> Start diagnosis" feature, this said, everything is fine. So, now I don't know, what to to?! I just want to have my calender synchronized!
Changing the files "ssleay32.dll" and "libeay32.dll" by updating OpenSSL or copying from the iTunes "http://...\Apple\Mobile Device Support"-Folder did not lead to any changes :-/.
I'm using iTunes v9.2.1.4, iPad iOS 3.2.1, Outlook 2003 SP3.
So is there someone having some more ideas or giving me a hint, where I maybe could read somthing about a possible error in a log or something like that? Maybe, only ONE appointment is "ill"; how could I detect it?
Regards, Andreas

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