Further comments...
Apple did a very nice job on this one. Once I got around the shared file problem, (iTunes requires the ._* files, for no good reason) I loaded about 4GB of tunes. In 8 minutes flat. ;)
The menus are very straightforward: Playlists (haven't done a thing with playlists yet) and two 'soup' views: Artists and Songs. Artists is actually the top of the Artist/Album/Song hierarchy. At the top of the Artist and Album levels are "All" entries that take you to the next level selecting everything. (IOW, Choosing Artists>All takes you to a list of albums sorted by artist. Artists>All>All takes you to a list of songs, sorted by artist then album.
Pressing the button in the center of the wheel descends the tree, pressing play starts playing from whatever leaf you have selected.
There are two other menus: Settings and About. Pressing the menu button always takes you to whatever leaf of the overall tree (settings or song menus) you last used.
Nice little features: Sleep timer, startup volume.
From what I can tell from a bit of surfing last night, the MP3's are protected from the file taxi functionality by nothing more than the 'hidden' bit. Utilities already exist to bypass.
Oddities: The 'clicker' (think beeps) comes from the unit itself, not through the headphones.
Gripes: The screen contrast with the backlight on is pretty poor. The backlight is way brighter than it has to be, as well. (These are probably the same problem.)
Oh, and I'm kinda done with Chicago, guys. Couldn't you have used Espy?
-Z