I transitioned a friend to ubuntu recently, he was sick and tired of getting viruses and the like. He is extremely satisfied so far.
He recently asked me if iTunes works for linux, because his girlfriend has an ipod. She likes to use the itunes store, so the usual amarok/rhythmbox solution doesnt work.
Unfortunately if you look at the wine application page for iTunes the rating is trash. Setting him up with virtualbox is just too extreme, he does not have a windows cd around.
The biggest thing is check what software they use regularly, and make sure it works first in wine or has a decent alternative. Otherwise they will just be disappointed.