I bought an iPod Nano for my wife, so she can listen to her music collection without having to turn on her computer. Never liked iTunes. It seems to take a long time to do anything and you have to wait when ejecting.
She got an iPhone 4S recently. I was pretty frustrated with it trying to move her contacts over from her old Galaxy Q. Moving her old ring tone was even more frustrating. I put her music on it since her iPod was dying. I had some difficulty syncing her music. It seems some new songs I put on her phone wasn't playing. They don't show up in her song list. I ended up having to make a playlist that included all songs before it could play all of her songs. Never figured out why some songs were missing.