Hi tmilbut,
Welcome to the Support Communities!
The information below may be able to answer your questions about how to delete items from a playlist on an iPod.
iPod Nano User Guide - Remove items from a playlist - page 23
http://manuals.info.apple.com/MANUALS/1000/MA1624/en_US/ipod_nano_user_guide.pdf
Remove items from a playlist:
1 On the Home screen, tap Music > Playlists, then tap the playlist you want to edit.
2 Flick down, then tap Edit.
3 Tap next to the item you want to delete, then tap Delete when it appears on the right.
4 When you finish, tap Done.
Delete a playlist:
1 On the Home screen, tap Music > Playlists.
2 Flick down, then tap Edit.
3 Tap next to the playlist you want to delete, then tap Delete when it appears next to the playlist.
If you tapped the wrong playlist, tap the one you want to remove.
4 Tap Delete, or tap Cancel if you change your mind.
5 When you finish, flick up, then tap Done (or swipe right to return to the Home screen if you cancel).
Cheers,
- Judy