I just got an iPod touch as a replacement for my PDA--not so much to play music, but more to check mail, read blogs and keep track of phone numbers and such.
So far, I'm very impressed with the iPod--the touchscreen keyboard works better than I'd expect, the interface is fantastic, and Safari is a much, much better browser than either Windows Mobile (an old version) or the one on my Palm T/X. The Stanza Ebook reader (a free download) is very nice. The ability to watch youtube is also a plus, although it would be nice if it were generic video rather than just youtube.
iTunes, on the other hand..well, since my Mom reads here, I can't give my full opionion, but "sucks" is the edited version. I can understand complexity in dealing with DRM, but I'm not--I should be able to treat the iPod as a thumb drive, and just dump MP3's into the proper folder. Instead, itUnes has to process them in a couple of passes before they can transfer.
...and using a separate Windows user account on my wife's computer still brings up her songs and such. By holding the shift when you launch, you can choose which existing user's ituneS to connect to, or create a new user but this should be the default on a separate user account. It appears that itunEs objects to being used with two computers--When I decided to try on my wife's box after giving up on the crappy computer I've got Windows on, it gave me the option to erase the ipod and start over, or do nothing.
...and apparently they have changed how iPods work enough that Linux hasn't caught up yet.