Been a Classic Ipod user pretty much ever since they came out. Use them (have 3...all 160GB models) all the time when driving...pretty much that is all I use them for unless I/we travel then I take one with me and set of nice ear buds... Great source for personal music. Use WAV files. It's like having CD's without all the hassle. Currently have 3245 "songs" (as Apple calls them) on them. Pretty much my "favorite" tracks. Every time I get my hand on a CD will give it a test listen pick the tracks (if any) I really like and "Import" (as Apple calls downloading...LOL) them into my I-Tunes. Love the way the "shuffle" option works now........used to keep playing a lot of the same "songs" over when in "shuffle" mode but looks like they have fixed that with the latest updates....now I hear pretty much different "songs" all the time now. Kind of like having your own little portable music server. All one needs is a cable with a USB on one end and the 30 pin connector on the other and you can pretty much play it through anything with a USB port.
I did find a really great Ipod dock a few years ago. The Phillips model SMJ3151/27. They don't make them anymore but you can still find them on e-bay and sites like that. What is nice about the remote is it has a small video screen and you can see everything your doing almost like a small computer screen. Very easy to "shuffle" anything, artists, genres, etc.... If youra "serious" Ipod user (just the 30 pin models) this is the IPod dock to have. See photo. (yeah it is a little on the large size...it is also a "universal" remote to control TV's, AVR's, etc....but it works great with the Ipods).