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.