HELP SYNC is Not working properly, very frustrated

I have a first gen I pod touch.
I just uninstalled Itunes 10.5.2.11 and installed 10.5.3.3
Untill just 3 days ago, everything worked fine.
Then I tried to create a play list for some videos and found out I could not do so.
Then I found out some of my play list files were not being transfered and some were.
So here is the problem
I have several play lists.
Bellemy
Workout
are just 2 of them. Bellemy is not syncing one of the 2 songs in that folder unless I check it. If I leave it unchecked, it will not appear in my play list in intunes after I sync my I pod.
The workout one, will only transfer all the songs, if I leave the ones the IPod has on it, unchecked in itunes.
This is really starting to get to me. Every time I have to do a software upgrade to this thing, or to the computer, something always goes wrong..
and I have no idea how to get my play lists to sync properly to my ipod touch.
Any help apprecated.

Hey Suresh1118,
Thanks for the question. I understand that you are experiencing issues with iTunes Authorization when syncing your iPhone. The following articles provide the most relevant troubleshooting:
iTunes repeatedly prompts to authorize computer to play iTunes Store purchases
http://support.apple.com/kb/TS1389
iTunes: Missing folder or incorrect permissions may prevent authorization
http://support.apple.com/kb/TS1277
Thanks,
Matt M.

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