Check this out
The 20 Best iPod Utilities. I've used HandBrake and it does a good job ripping DVD's to iPod. At quick glance, I'd like to try the Last.Fm service so I can get recommendations on music I'm listening to. Interesting to see a Rockbox firmware replacement for iPod. I used Rockbox on my old mp3 player from Archos. There were some cool features there that I liked but it seems ages ago.
Can't wait to get some time to try some of these. Cool goodies and mostly free.