Well.. yes and no. You can start a new library. Copy all the iTunes “caressed” files to your external library (you have a back up anyway, right?) and then add the files back in. Not a small task, but at least then you have a consolidated library.

Aha.. Turn off the option that lets iTunes manage your MP3 library. iTunes then uses the *original* file that you imported into iTunes. This was about the first thing I did when I got my 60GB Video iPod 2 years ago, because I used 2 seperate machines to sync music (one at work, one at home) and pretty much don’t back up anything on the iPod. The only stuff I tend to back up is the stuff I buy electronically.

I really, really, hate what Apple does with the syncing thing on the iPhone.

I do something similar but slightly different: I sync that playlist in addition to a few other playlists. So in my case, it’s “whatever’s on that playlist is guaranteed to be on the phone, but there might be other things on there, too”. I find it works pretty well for my usage needs.

(One of the playlists I sync is a “rated highly but haven’t listened to in a while” smart playlist, which I kind of like. Works well with the double-click-the-headphone nub-to-go-to-the-next-song feature when the phone’s on shuffle; helps me discover some music.)