Especially when there are tutorials and everything else to help with iTunes. Don't get me wrong; it wasn't easy switching to syncing an iPod when I was used to Windows Media, but I figured it out. Some people I swear think that if they even touch their mouse they will break something
Both of my parents have issues with iTunes, even after years of owning iPods... Thankfully they are fine with other computer things. My dad works on a computer all day with programs and what not. And my mom teaches a computer class among other things.
Honestly, I'm probably the person who knows least about computers in my family.