One of the latest projects I am working on is ripping a DVD (which is legal because we own the DVD and the contents on it) and transcoding it for use and viewing on the web. The final product is almost 2 hours long, so we are still tweaking with size versus quality. Here are the tools you will need in your corner to get the ripping started.
First I used a freeware (cross-platform) program called Handbrake. I ripped and transcoded each chapter into an .mp4 file (because of the quality and size compression). Handbrake could not read the last chapter on my DVD, and sometimes would get buggy and not read all of the DVD chapters when I restarted the program. I downloaded another program called Mac The Ripper. This program also rips DVDs but it is only available for Mac OS. I ripped the last chapter as a VOB. I had to use the "Title-Chapter Extraction" mode because Mac the Ripper kept getting a "Bad Sector" error when trying to rip from the DVD (cleaning the surface of the DVD might help). Mac the Ripper is also a great tool if your DVD is encrypted (I am in no way advocating pirating DVDs).
After getting the VOB file from Mac the Ripper, I opened the VOB into FFMpegX to transcode it into an .mp4 file. Even though FFMpegX does the trick most of the time, the file that you receive as an end product can be twice the size than it should be. Also it requires you to purchase the mpeg2 encoder from Apple to get the full fuction out of the software. My goal in this project was to not spend any money unless I had to, and I ended up not having to.
I brought the .mp4 files into iMovie HD (iMovie-the regular edition doesn't allow you to import .mp4 files). From there I joined the movie clips into the time lines and hit share and used expert settings to input the settings I wanted.
Before I realized iMovie HD had the ability to import .mp4 files, I was taking the .mp4 files I ripped using Handbrake, and transcoded them into .avi files using FFMpegX. I wanted to use movie joiner programs that were freeware on the PC. The files imported fine and the movies seem to join together correctly, until I realized the sound was off and not in-sync with the video. There was no way I could edit the audio inside the programs and the two I used were trial versions of the programs. Hope my trials help you in the future. Here are links to the programs I used:
FFMpegX (Mac Only?, plenty of programs like this for PC)
iMovie HD (Mac Only, comes with Mac OS X in the iLife suite)