My iPod's hard drive crapped out, so I can't answer that question with certainty. Here's my guess: no, not if you delete them within iTunes. However, if you delete the respective files manually (e.g., Using Windows Explorer or Mac OS X Finder) this should "con" iTunes into thinking they're still there, and they'll still show up in iTunes (being stored in its database) and you should then be fine. Try it with one song or something.
And I'm always willing to give out tips and help.
