Off Topic Ipod Help

You could do him a mix tape.

 

I grew tired of always having to lugg a biro around with me, for manual tape winding after its spewed out.

My best of Extreme is ruined now.

 

I have Pornograffitti somewhere on CD

 

I'm jealous, More Than Words.

 

There's no function in iTunes that does that, for obvious reasons.

As others have said the third party software should do the trick.

If you still have the old computer, just back up the library from iTunes to an external drive and transfer them across, that way you have a back-up as well if anything goes wrong with your computer/iPod.