I am surprised at all the trouble with iPods and iTunes. We have 5 iPods in the family, 2 30 GB video 5th Gen iPods for my wife and I, a 4gb nano for my 8 year old, a 2nd gen shuffle for my 6 year old, and a 1st gen shuffle for my 3 year old. We have not had problems - even my young kids use these things without problems. They are all used regularly, from everything from homeschooling work to listening to audio lectures and stories.
iTunes is great - very intuitive and works well. It is stellar compared to a program I tried to use for another MP3 player.
Typical Apple program: if you use iTunes solely on all default settings, never change the location of your library, never use an external hard drive, and basically let it completely control your digital music life, it works fine. If you try and change anything, it blows up. Everybody thinks MS is Big Brother, but Apple is double-plus-good.