A CD takes about five to ten minutes to upload into iTunes.
Once the files are in iTunes, it's just a matter of dragging and dropping them onto the iPod which won't take more than a few minutes.
When you import the audio into iTunes, as long as your computer is hooked up to the internet, iTunes will fill in most of the data about the CDs assuming the albums are registered in the database. I often have to tweak things a little bit to fit my categories, which can be done quite easily by selecting the track/album in question and going to File>Get Info.
I suggest getting the largest iPod you can possibly get. I have the 160gb and it's very convenient to have built a representation of my entire collection on one device. Still, you could easily fit 200 albums on an iPod a quarter of that size.