View From The Box

I adore electronics. I inherited it from my dad. I've been contemplating iPods lately. I need long distance music in my car - which came with nothing but an AM-FM radio. So much for car shopping in Vermont, but we'll save that for a different rant.
Input would be welcome. Is 30gb enough? Is 60gb insanely big? By the time I get the iPod and the dock and the radio transmitter this is turning into quite a proposition. Since there's no cassette deck in the car, I *have* to use the fm transmitter option. I already have a Belkin transmitter that I use with a CD player. Will this work, or am I committing myself to yet another piece of stuff to carry around? How many hours am I going to spend d/l or copying music off my cd collection? Is anyone out there using the non-Mac mp3 players and what do you think of them? How fragile are any of them?