This is a very old topic I read some years ago, and I now use the method it described. I couldn't find it in the forum, so I'll try to explain very quickly how I proceed. If you need more information (depends on how deep you know MC), I'll try to bring you more details later. It may not be exactly the same but it works pretty well...
- Basically, you need to create two library fields, one for each iPod. (Options -> Library & Folders -> User library Fields)
- For each song, you'll set that field to a value meaning that you want that song on the corresponding iPod (1 if you want it, 0 if not). You can set up custom view schemes to easily set the values (using tagging mode for example), display a columns showing the value of the fields, etc.
- Then you build two smartlist based on each new field : each smartlist will contain only the files you want on each iPod.
- At last you configure each iPod to sync with the corresponding smartlist.
Ok I made some screenshots because I'm not sure my explanations are very clear
Field creation :
View Scheme :
Smartlist :
iPod settings :
Hope that will help...