iPod ripping dvds to ipod classic

[sportsfan27]

I have a 1.4 ghz iBook G4 running Tiger and I'm trying to rip a few DVD movies I have (legally) purchased to my 80GB iPod Classic. I've been trying for months to figure out how to do this. First I used the DVD to iPod software from IMToo, but after several email conversations with their tech support, all it did was create a file that wasn't playable in iTunes or Quicktime. Next, I used Mac the Ripper, but the resulting .vob file was only about half the size of the DVD and when I tried to convert it in MPEG Streamclip, it said it was "unable to locate the first frame." I also tried to convert the file in iSquint, but it created a 32KB file that played a blank image. Next, I downloaded Handbrake, but it was also unable to rip the DVD. I then tried to convert the .vob file from Mac the Ripper in Handbrake, but the file was only about 20 mins of the movie. I've looked into hardware instead of software, but the only device I found that can rip protected DVDs is the iRecord, and I am reluctant to pay $200 for it. Do you have any suggestions as to what I should do? Thanks in advance