Matching against TheTVDB

Gilmore Girls A Year in the Life: Gilmore Girls: A Year in the Life - TheTVDB.com
and as such:

A TV Show Library/
…Gilmore Girls A Year in the Life/
…Season 01/
…Gilmore Girls A Year in the Life - S01E01 - Winter.XXX
…Gilmore Girls A Year in the LIfe - S01E02 - Episode Name Optional.XXX

Filebot could have handled that lookup and naming almost instantly (link in my signature).

Caveat:
If using MP4/M4V files bogus embedded nonsense in the Title Field will result in a bogus match. The solution is to remove said nonsense from MP4/M4V files or simply Move Local Media Assets to the bottom of every Agent List you can lay your hands on (drag and drop to the bottom of the Agent Lists):
https://support.plex.tv/hc/en-us/articles/200241558-Agents

For best results:

The Plex Dance®:

  1. remove show from library
  2. update library
  3. clean bundles
  4. empty trash
    https://support.plex.tv/hc/en-us/articles/200392106-Library-Actions <------ update libraries, clean bundles, empty trash
  5. rename/restructure Show/Episodes
  6. replace show into library
  7. update libraries

… as my test file sits in a TV Show Library:
F:\MCEB-TV\Gilmore Girls A Year in the Life\Season 01\Gilmore Girls A Year in the Life - S01E01 - Winter.mp4