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Its been a minute since I've used Plex so I don't remember the exact specifications, but I set up a separate library in Plex and directed it to my YouTube folder where I had everything pre-organized, and then I selected the option in Plex that was something like "show folders," which organized the Plex library the way I had the directory organized. It wasn't perfect because I had to set up everything manually, but all I wanted was to be able to watch my YouTube videos from anywhere in the house, and for that it was perfect.