My 2 cents for the iPod.
I have the "little" iPod Nano 4gb model.
I like it fine for music.
It has great capacity. Mine has nearly 650 songs on it.
It has room for several hundred more.
I would like to have one of the bigger ones for movies, etc.
But, I believe that I could drive from Kansas City to Colorado Springs and not hear too many repeats. (I'll be testing that out next month)
On the downside, the battery life on the iPod is kinda short.
I play mine constantly in the car, 40+ minutes each way, and hook it up to the stereo in my office. I have to charge it about every other day. I could likely go to every third day.
I rarely use the earbuds. And the earbuds can get LOUD!! So, you don't have to turn them up too loud.
But when hooked up to a car stereo, or destop unit, it has to be turned up pretty loud which burns up the battery a bit quicker.
But, mostly, it rocks.
It is also really easy for old duffers like me to figure out how to download stuff. Granted, all my stuff is albums. I haven't bought any music from iTunes.
However, to play it on the car stereo you have to either have a newer car with a hook up, an aftermarket stereo with a hook up, or one of the radio transmitters that is powered by the one of the car's power points.
And those run from about 20 - 80 bucks. And they are only "fair to middling" function wise. I find myself changing the station mine transmits to several times during my commute to get rid of static.