Theres no iPod that doesn't do those things... you'd be hard pressed to find any player with a HDD that doesn't do those things anyway... they're kind of like cell phones and SMS and cameras now.

I'd personally just get an 80/160GB iPod and call it a day.. they're big (80 gigs in my world is something like 45 days of straight music.. wayyy more if you like your music @ 160k or lower) and iTunes/iPods are both pretty refined [short of iTunes hogging ram... but it's worth it imho]
it's just a case of teaching old dogs new tricks.... think of it this way, every song you own gets put in your library. instead of having a "mix" you rather order the songs you want in a playlist. if the album loaded into the library is a mix it's considered a compilation and can be marked as such (that way it's listed under the artist "compilations" and then under the respective album name)

and as always remember going from cd->mp3->cd->mp3 is highly advised against, as multiple times of doing this will leave a person with nothing but garbage quality

 

how does itunes work? Can you download mp3's from wherever (i.e. :rick: ) and still get them onto your ipod? Or do you even have to use itunes?

 

You can load the songs from anywhere. They have to be in AAC, MPEG Audio, or WAV formats (there may be more now, it's been a while since I've checked up). This means that protected WMA files won't play at all.. and unprotected ones will have to be Xcoded with the usually loss of quality.

Other than that it's pretty much up to whatever you have to put in there. As always I suggest finding a using full albums over anything else.

 

I have a zune, I like it. 30gb $100 and rather large screen.

 

i'd suggest this except I download on average about 3 gigs of music a month, though i guess I am kind of on the extreme side of things it sounds like he may be getting more than the zunes can hold...plus WMP is miles behind iTunes IMO

currently the biggest zune is 80GB

 

winamp supports ipods