|"Any other tips?"|
As you become more familiar with ripping, you might find out that files ripped to a lower bit-rate (i.e. 320KB vs 128KB---assuming it's .mp3's) are difficult to distinguish, especially in a moving car. You might want to try some items at both. Likely the 128KB is significantly smaller than the 320KB (allowing you to get the aforementioned more songs on the drive). I don't have a car stereo that can handle USB drives directly (a '95 Saturn with a cassette deck), but I personally rip stuff down to 56KB @ 22KHz. This gives me most songs at 1-3MB each. I put them on my Droid phone and play thru the cassette deck with an adapter. I have over 90 albums that I carry with me at all times.
"Channeling the spirit of jboy..."