Hmmmm.... forcing something into Audiobooks, not sure how to do that. There might be a way with some scripting stuff.
Ripping DVDs is doable, but a little tedious. DVDs contain copy-protection stuff on them that deliberately makes it difficult. Under some of the more recent revisions ot the copyright laws in some countries (such as the "DMCA" in the US), it could actually be illegal to copy off the data.
Personally, I think that's nonsense. I think its only sensible that someone should be able to make personal use copies of content they have paid for.
And so, I have done it and here is the procedure I use:
(1) DECRYPT. I use a piece of software called "DVD Decrypter" for Windows to undo the copy-protection nonsense. You can choose individual chapters/titles to decrypt off the disk, or do the whole thing in one file. You may have a hard time finding this software online, as the author of it was threatened with legal action, and no longer maintains it. There are other similar packages for Mac, but likewise they tend to get sued out of existence, so make sure to keep a copy of the install files when you find one.
(2) CONVERT. The output of DVD Decrypter is a "VOB" file, which is basically the same sort of data that is on the DVD itself. You need to convert this to something that the iPod can read. I use a command-line program called FFMPEG that is open source and free, to do the conversion. Go to ffmpeg dot sourceforge dot net to download a copy (I'm a noob and can't post a link yet).
(3) CHOOSE RESOLUTION. For the iPod to read it, you'll want to convert to MP4 file, and use either the mpeg4 or H.264 codec for the video, and AAC for the audio. Now the native screen resolution of the IPOD is 320x240, so if you are only ever going to view it on the IPOD screen itself, use that. HOWEVER, if you ever plan to also view the video on your PC in iTunes, or via a cable from the iPod to a TV, then you can actually encode to 640x480 for better picture. This only works if your ipod is the latest 5G or 5.5G 'video' model, and you have the latest firmware loaded on it. If you choose to go 640x480, then you MUST choose the mpeg4 codec, and you must limit your audio quality to 64kbps, due to limitations in the hardware of the ipod.
(4) Here's a sample FFMPEG command line I use for encoding video to 640x480 ipod-compatible format:
ffmpeg -y -i INPUTFILEHERE -vcodec mpeg4 -f mp4 -b 2000 -s 640x480 -aspect 4:3 -acodec aac -ac 2 -ab 64 OUTPUTFILEHERE
(5) Once you have the files converted, you can drag and drop them into itunes, or choose File | Add File to Library... from the iTunes menu.
Hope that helps. Again, the lawyers have made it tedious, but not impossible.
--Tim Farley