Out-of-the-box, with a new "third generation" iPod (the ones with the dock connector on the bottom and the backlit buttons) goes like this:
1. put in the CD and cancel EVERYTHING that autopops.
2. search the CD for "updater.exe" -- copy it to your desktop or wherever you'd like to store it.
3. Plug in and run updater.exe. Use it to "restore" your iPod.
-- see, the iPod comes out of the box formatted HFS+ for a Mac. You MUST run this updater, which will format it FAT32 for windows.
4. Once the restore is done, fire up MC9. Go to the "CD, DVD, and Handhelds" section and look for a little palm-pilot style icon (ahem, Steve,
). Click it and you may get a "you need to format your iPod" message. Do so.
-- "formatting" with MC doesn't format the drive, like the updater does. Rather, it just clears out the iPod_Control folder and recreates pertinant data. You'll only have to do this once, if everything works well, and it takes just a second to do.
5. Right-click the iPod, select synchronize, and then just put a tick in the box next to each playlist you want to appear on your iPod.
6. After a sync, each playlist and smartlist that you sync will be on your iPod, along with (only one copy of) each song called out on these playlists.
It's remarkably fast, easy, and smooth. Enjoy!!