If I still had an ipods or iphones, I would investigate a third party sync tool and find one that could easily sync a folder full of music files to my i-devices. Then I would use MC's handheld sync system, to sync playlists, over to that folder (including the music files of course). Finally, I'd use the i-device sync tool to sync the folder to my device.
The itunes integration all seems too complex to me. But, then again, I haven't tried it. I've spent probably 3 to 5 hours over the past year researching it at various times to try to help people. But I haven't done it myself; just read about it.
Glynor has a complex way of syncing his MC to a separate computer where he maintains an itunes library; just for syncing iphones I believe.
Brian.