As explained in PM, there is always an option of Smartplaylists. BUT the songs must already be within the iTunes Music Library.
Just received your 2nd PM as I was about to reply. lol Ok so iPod is not reading your iTunes playlists at all. That's odd. They should work after all iPods were designed to work around playlists in iTunes 'if' the songs are actually within the iTunes Music Library. Check
How to transfer music to my iPod (& iTunes) {click on link} & the links within to the Mac iPod tutorials. I think they might be near bottom of page. I supplied my own copies of the videos for manually updating the iPod because Apple decided to remove their previous videos from their site. Oh here the QuickTime Tutorials:
http://www.gnutellaforums.com/open-d...tml#post129776 such as manually adding. And recheck their instructions for playlist adding. They do seem to have something odd with the new iTunes. I do have old iTunes versions around.
Double-check all the songs in your playlist to be sure all songs play. There are some duds going around. They might be corrupting your attempts to get the songs onto iPod.
Here's part of what I was going to post: (a)
http://www.gnutellaforums.com/321049-post8.html
(b) image below shows another type of playlist.
