You can then rip and convert new movies with handbrake if you like, but I stopped caring about saving 1 or 2 GB when it saved me the hassle of all the conversion setup and wait time. This will give you a single file to name properly for Plex and save you loads of time. If space is not an issue, and you have all the DVDs ripped already I would recommend something like MakeMKV it will just encapsulate the movie vobs into a MKV container. With several hundred DVDs you will be at this conversion process for quite some time. Handbrake is great if you want to save a ton of space and convert the vob files to a single file, but this takes forever to process. I was able to rip my DVD collection much faster then I was able to convert them to useable single file formats. I have run into the same issue as you in a sense.
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