I've done this for years with no problem, but with the updated iTunes, it's difficult and the ipod download is scrambled --all the first tracks play, then all the 2nd tracks, etc. Hope this is posted in the right category...? Thanks!
You posted in the correct place. The updated version of iTunes did not change the way your music is played or synced. First make sure that none of the settings on your iPod have changed. It sounds like there may either be a problem with your music library or with the sync from iTunes to your iPod.
Since you're using Windows, please see the following Apple Discussion Topic and follow their directions to repair your music library: Go to this LINK.
Shop for your Apple, Mac, iPhone and other computer products on Amazon.
We are a participant in the Amazon Services LLC Associates Program, an affiliate program designed to provide a means for us to earn fees by linking to Amazon and affiliated sites.