Ubuntu Plex recognized everything correctly except for my TV shows

Whenever I plug the USB into Ubuntu it’s auto-mounted to /media/<user_name>/PLEX8TB

This is what you need to fix.

The automounter mounts with exclusive access to your username ONLY.
Username plex will not be allowed to read the data no matter any permissions you might apply.

To rememdy this, define the mount point in /etc/fstab
Linux supports mount by UUID= and LABEL= identification. This works well for USB devices because the /dev/sd* letter will change each time it’s removed and reinserted.

In this example, I show how to handle different cases.

Adapt to suit your needs;

  1. Pick a mount point which doesn’t interfere with any existing directories
  2. use blkid to get the UUID info.
  3. Create the /etc/fstab entry to find it.

When done, the drive will always appear at the same mount point each time WITH the permissions you’ve set and Plex will be able to access it.