Buy a Mac. :D

That said...

If you're looking at Debian on a desktop, I'd look at Ubuntu instead.
Ubuntu is such a nice desktop, and the release cycle keeps things up
to date better than Debian.

iPod is no big deal. It is a USB hard drive, and shows up as such
under Linux. There are various Linux applications for managing the
music on your iPod, so you're basically in the clear as long as you
don't have DRMed music from ITMS, Audible, etc.

www.yamipod.com is the first app I came up with while googling, but
I'm sure there are others. Just search for ipod on freshmeat.net.


--
Andrew S. Zbikowski | http://andy.zibnet.us
SELECT * FROM users WHERE clue >0;
0 rows returned