try
CDex for the cd ripping to MP3. It is pretty intuitive, and free.
more info on it:
CDex - Wikipedia, the free encyclopedia
I personally never got an ipod because I've been working at home for the last few years and never had a situation for it (ie. 45 min train rides into the city). I guess if I needed a way to store thousands of songs to play in the car then I'd get it, but I don't have that much music either. If you do, that's probably the best way.