Quote Originally Posted by Ritamarie View Post
Isn't there some kind of wireless gadget that you can use with the car stereo where you tune the car stereo to a certain frequency and it picks it up?
There is, but sound quality isn't that great. If his car doesn't have an input, I'd at least find out how much it would take to install one, before buying an FM transmitter.

So is the Nano good for all of this? Or should I get one of the classics?
Depends on how big your library is (and related, whether he would keep the music at a higher bit-rate if he had the capacity for it). The Nano maxes out at 16GB, while the Classic is 160GB for $70 more. If 16 GB is enough for him, and he won't be using it for anything but music, the Nano would be fine. http://www.apple.com/ipod/compare-ipod-models/