TV Naming convention for grouping personal media files

TV Show Library is correct.
Fix Match/Search Options/Agent/Personal Media
That will tell Plex this is a Personal Item - and Plex won’t mess you up trying to match it. <— or Blow your Edits when it does - and it will.

Now you’ve done that - there is no way to get exactly what you want, but you can do this:

A TV Show Library Folder/
.......Family Movie Time/ <---whatever you want here
...........Season 2019/ <---the most obvious is a year type season, but you pick
.............Family Movie Time - S2019E01 - Christmas at Mom's.xxx
.............Family Movie Time - S2019E02 - Christmas at Dad's.xxx
............and so on...

There are limits to what you can do and you must stick very close to the TV Show rules of behavior for naming and structuring - ‘very close’ means ‘exactly’ - if you want Plex to work.

No, Plex won’t take that ‘Episode Name’ from the file, but when you are hand editing this ‘Show’ you’ll edit those in rather quickly.

You can, of course make a ‘Show’ all about Christmas - or any other ‘Show’ you want.

The “Season” can have a text description in the Edit thusly - I just put this one in, for example:

One way or another you can get where you want to go - perhaps not on the path you’re currently on, but… you can get there…