I have a Nano that I still use on occasion (it's ridiculously small - 8 GB - so I only use it if I need something specific, like if I'm going to see Flying Colors, I'll put all the FC on there) and I'm still able to use it with iTunes, though I'm also not on the most recent version of iTunes. The latest upgrade is whack, if you ask me, so while I'm still doing my ripping project (see other thread; I'm putting all my music in lossless format onto a separate hard drive) I'm going to keep the older version. If and when I'm forced to upgrade I'll have to figure it out.