The latest version of iTunes still supports your iPod Classic. The freezing could be an indication of a corrupted or damaged hard drive in your iPod. I would recommend doing a disk diagnostic on the iPod's HD using the instructions given by turingtest2 in this older thread. He also covers what the resulting numbers indicate.
If necessary, post the resultings numbers and we can verify what the next steps to take.
Pending Sectors: 16
PowerOn Hours: 123
Temp: Current 25c
Temp: Min 3c
Temp: Max 50c
Doesn't look good. Should I follow the steps to repair the disk? Also, should I revert/restor to the most current version of iTunes before doing this process?
Thanks in advance.
I should have kept better notes, but some how between the repair disk and erase and sync magic occured. It tryed to sync and came back erased - oh crap- them I went for broke and repaired/erased/restored. Then itunes recognized it as a new ipod, started over and boom synced and fixed. I don't plan on plugging it is very often.