I understood the frustration. Even with fairly sophisticated tools, it can be pain to convert files from one kind to another. Currently, my project is to convert a VHS to MP3. The video is old and unnecessary. My mom thinks the content is great, but would rather read it. So... how do we go about transferring a VHS to text? Here's what I've finally come up with:
Step 1: We have a VHS player that automatically copies to DVD. Cake.
I dropped my DVD into my computer and tried to rip the audio straight out. No can do. The video files are a jumbled mess of multiple files that do not play sequentially. In fact, I was unable to find the start point anywhere.

Messy DVD Files
Step 2: Open DVD in DVDShrink and "Backup!" the "Main Movie Title" from the DVD.

This makes the once four separate VTS files into one.

Step 3: Fire up VLC and "Convert/Save" to an .mp3 file.

Step 4: (optional) Open the .mp3 in Audacity for further cleanup/editing and export.

I believe the plan is to play the audio to a dictation program which will-theoretically--convert it to text. Here's hoping!
~Luke Holzmann
Your Media Production Mentor