this is the best place I have found for answering any questions regarding anything ipod or itunes related. The Ilounge forums. http://www.ilounge.com/ go there click on forums and ask, they will probably be able to help you. I avoid all things ipod and itunes related!

Weird, I think I'd post direct to the Itunes Windows forum on that one. Here is a link that might be useful: Discussions apple

iphones have interfaced with gmail and Google apps for a good while, despite the natural tension between the two. I have a couple of family members who use Iphones, gmail, and PCs. I don't think the sync between PCs and google works as well as before, like for calendars. Your friend may need to adapt her work flow to be her smartphone and the Google site in a browser instead of her pc. I think there are IOS apps for gmail, calendar, contacts, that do the trick. Do some Googling and also check out the very active Apple forums, I think you'll find an easy solution. Or, if your friend has Apple support, call them or visit an Apple store.

A bit late to this, but did you try calling the iPod tech support number yet? I did that when I got my new iPod (shuffle) & the young man was very nice & helpful; did a shared desktop screen while on the phone as well, where he showed me w/ pointers what to do & what to click. (side note: I believe new devices from Mac are just not as intuitive as they once were. I never had to get help w/ my old iPod) Do you know how to make a screenshot? Showing what your screen looks can be helpful for stuff like this. You should be able to do a search of your computer for the iTunes folder, shouldn't you? When I've purchased Amazon MP3s, I simply dragged them into the iTunes icon on the desktop(dock) & then drag those files into the iPod - which shows up in the sidebar of the iTunes screen. I'm on iMac, tho - no experience how the Windows version of this works... FWIW, HTH