[JerseyHighlander]

Don't know of any program specific, but

There are programs avilable to scrub (or replace) file attribute fields in bulk.

So, manually scrubbing the pc hdd files of the last played field before transfers to IPod could do the trick.

Also

I think ITunes has a "search for duplicates" option in it. I know that fixed a similar problem I had.

[martin_fierro]

Yeah, I currently use a free Java-based app called "Seek and Destroy Music Duplicates" by Pekarna, but wanted to kow if there was a way to tweak iTunes to prevent the file duplication from happening in the first place.