Skip, Skip, Skippin Ipod!

So, I've had my iPod classic for maybe... 4 or 5 years. So I realize there ARE gonna be some problems with it now that it's a little bit older and I don't have anymore I insurance on it. =/ My problem is, since year 3 or 4, now it wants to start skipping songs. Downloading new itunes music was fine maybe 2 years ago. Now it seems that every purchased song-mind you old AND new-wanna start skipping. It could have something to do with my computer, but I've never had this problem before.

What's going is it will play a purchased song, and stop and then repeat the song over or go to the next one (depending on if I have repeat on) and it does that all the TIME. So I figured out how to fix the song problems and that was to create the AAC version for the song and delete the original one out of my iTunes. Worked like a charm. But NOW, it's doing this pause and repeat thing to my movies! I just recently got the Transformers 2 (Which I LOVE) and it paused and repeated on 2 different times. Twice I had to speed past those parts and the rest of the movie played well up to the end. I tried to do the AAC version thing but it won't let me for security reasons. It plays fine in iTunes but it won't play without skipping on my iPod. Someone tell me how to fix this thing before I strangle the electricity outta my iPod!