I've been ripping my DVD's with a free program called Handbrake on my MacBook Pro, but I think it's Windows compatible also. It's dead simple, put in DVD, choose Ipod Hi-Rez output, and click start....then about 1.5 hours later, you have a full copy of the DVD in MPEG4 format, which you can then import into Itunes, and sync to Ipod
I've prepared some ready for my 160Gb being delivered this morning, and they look amazing on the screen
I'm not a big fan of Handbrake for Windows - the Mac version is very good, but the Windows version is lagging behind in development somewhat, and I find it a bit flaky.
I use a free program called Videora - this is pretty quick (about 1/3 real time on a 2.4 GHz Core Duo) and produces nice results. The user interface is a bit quirky, but it's good under the hood, and seems (for me) to work more reliably than Handbrake.
For both Videora and Handbrake, you will also need some way of removing the CSS protection and copying the disc to your hard drive - DVD Decrypter is good for this.
I transferred Pink Floyd's Pulse DVD last night using Videora, and it looks fantastic on my classic.