If only the iPod had native FLAC and/or drag-and-drop support, it would make the Classic utterly enticing.
Otherwise, it's too much of a hassle for me to use. (Even though I use Rockbox, its GUI is way too ugly.)
My library is in FLAC, so I can either directly import it (if it supported FLAC) or have Foobar convert FLAC files on the fly (if it supported drag-and-drop).