Looking at your logs I believe you have (had) two versions of this file…
Mar 14, 2022 12:34:45.664 [0x7fe6f2a8eb38] ERROR - Error opening file '"/mnt/md0/TV Shows/The Simpsons/Season 33/The Simpsons - S33E14 - You Won't Believe What This Episode is About - Act Three Will Shock You! WEBDL-720p.mkv"' - No such file or directory (2)
and
Mar 14, 2022 12:35:05.354 [0x7fe6f2718b38] DEBUG - Looking for path match for [/mnt/md0/TV Shows/The Simpsons/Season 33/The Simpsons - S33E14 - You Won't Believe What This Episode is About - Act Three Will Shock You! WEBDL-720p Proper.mkv]
I also see this error …
Mar 14, 2022 12:34:54.034 [0x7fe6f2a8eb38] ERROR - Couldn't find the file to stream: /mnt/md0/TV Shows/The Simpsons/Season 33/The Simpsons - S33E14 - You Won't Believe What This Episode is About - Act Three Will Shock You! WEBDL-720p.mkv
I suspect you need to empty your trash as plex most likely needs to delete this reference to the old file after you added a different later version. You may even need to plex dance the episode/show.
