I am not trying to be repetative but I do have a specific ipod bug you might want to check out.
When synching my 4g 20gig ipod using a custom smartlist the tracks in the ipod file system double up.
for example, reinitialize the ipod, sync with smartlist, detach the ipod change some file in the smartlist, resync, now there are two instances of every file in the ipod. These are not physical instances because there was allready 18gigs worth on the ipod before the second sync. So plug it back in for a resync and then you have three versions of evry file...etc.
I do have another small related bug which i though had been fixed but seems to have reappeared, when dragging files from one pane to another in order to tag them if there is info in the tag and you drag to unasigned nothing happens, if you drag to another tag (from yes to no for example) then the existing tag is erased but not rewritten with new info. I use this method for syncing my ipod which is why they are related for me.