I was told by plex on twitter to post about the transcoder was unable to process this media error

If you don’t place the videos and the subtitle in their own folder, every file has to be scanned. Any glitch will prevent the subtitles from being added/removed.
Plex may still think the subtitle is there even after you deleted the file. You can double check this by reviewing the XML. https://support.plex.tv/hc/en-us/articles/201998867-Investigate-Media-Information-and-Formats

You can also Plex Dance the file to reset what PMS thinks about the file and any subtitles. https://forums.plex.tv/discussion/comment/908454/#Comment_908454