nd-extras/ installed, scanning the library will almost pick the proper file as the movie, and the remaining files as "extras". This works well for me: As long as the original ISO filenames are reasonable and I have. When you run the script you select the ISO files of interest and it puts the largest resulting MKV file into "MKVs/diskname", the others into "MKVs/diskname/Other", and moves the original ISO file into "Converted for Plex". It assumes that you have your ISO files in a folder that also contains a folder called "MKVs" (where the results will go) and another called "Converted for Plex". It's not fancy or robust, perhaps more of a starting point for others. It wasn't clear to me that there was a good way to convert a bunch of ISO files to MKVs in a way that works well for Plex on Mac, so I created the attached Automator workflow.
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