Well not the cheap way to go but I got an iPod for my birtday and
yes the icon give a hint of what I think of it (I love it!)

I do have the cassette car adapter in the car and I plug it into the iPod
headphone jack. It is easy to use and set up (even on the windows side of things).
My only drawback with it is that the battery life (before recharging) is 8 hours. The
new 4th generation iPods which are just out the battery life is 12 hours. Mine is the 15gb size
and I am not even close to filling it, but to give you an example I have 23 hours worth of
music on it already. I works great for the trip up to and back from Petaluma.

For downloading I use iTunes (which makes it easy to load songs into the iPod) and I
use emusic.com. iTunes you can buy individual songs for 99 cents and with emusic it is
a subscrition (I think it is 8 bucks a month with 50 downloads, its daltong's account that we share).

As far taking music from your tapes that should be easy to do, and is legal. There
is part of the Electronic....and then I can't remember what the name of the law is
that states you can make a "back up copy" of software, music etc. so taking stuff
from one media and converting it to another, as long as you paid for it originally, is
legal.

If you have any other questions let me know