That some wild scanner log contents - can’t really make heads or tails of it - but I can see your naming and structuring is so far off the beaten path if you were to say it’s not working, I’d believe you. What I see simply can’t work.
@BigWheel will get you all fixed up.
I wouldn’t know where to start so I would suggest starting over AFTER reading these:
https://support.plex.tv/hc/en-us/categories/200028098-Media-Preparation
https://support.plex.tv/hc/en-us/articles/200220687-Naming-Series-Season-Based-TV-Shows
https://support.plex.tv/hc/en-us/articles/200381023-Naming-Movie-files
