ever tried a Mini-Disc
the best thing i ever bought i tell, you it sounds like just what ur looking for. although an ipod is good too. MD is my absoulte reccomendation don't bother with anyhting else.
they can have upto 5hrs on one disc

, totally re-recordable, move and erase tracks, rename, blah blah blah.
don't get a car MD-player or changer, way too 2_cents !!! get a cd player or changer with a auxilery input. then plug in ur MD walkman (or what ever) via the headphone jack. and ta da, very high quality sound and change it asmuch as you want, no compatiblity probs like CD-Rs etc. dance
what you are after is a sony LONG PLAY Mini-Disc walkman, before LP there wasn' much point to a MD. now the 74/80min discs (smaller than a PC floppy disk) can hold either 2x (use tis for CDs u luv) or 4x (use this for so so CDs and radio) as their capacity!
the thing is the setup. best to have a:
car CD changer with aux in $300? (face unit only, no changer)
MD walkman - recordable LP $420 basic
audio sys at home with aux/CD out so you can record from the MD walkman.
or better still
MD mini hifi - recordable LP $600 basic
hi speed dubbing from CD to MD - digital blah blah
i bought a basic LP rec MD walkman in singapore for AUD$270. don't bother with the fancy ones, they do the same thing, trust me. and if you wait till sony are about to replace the models then you can pick one up for what i did in singapore!
then i waited a year or so till my mini-hifi kicked the bucket

and saved to buy a new MD mini-HiFi and have an excellent setup! dance
but you can start with a car audio with aux in & a rec MD walkman. it took some time to get to the setup i have now but its great!
why dont' you try a new CD changer face with the old changer first, see if you get lucky???