I sometimes have these stubborn matching problems where I manually unmatch, then fix the match… If I then move the file and rescan, the file match has to be fixed again. I know I can improve matching by changing file and folder naming but is there another way? Ideally I’d like to drop some kind of ID file that forces a match or naming somehow to give a better hint to the media scanner. This would be particularly helpful to specify naming and image icons for personal media that will never match an IMDB listing.
Those should be put into a library of the type Other Videos and will as such not do any matching
Then I can’t create seasons, can I? Example: a bunch of old coding training videos… There’s maybe 8 sections (seasons, if you will) and 20 videos for each season. How does that work with using “other videos” category?
Bonus question: can you drop an image with a standard naming (e.g. cover.jpg) to override the icon image used for a given video?
Well, you could you a combo of Collections and Playlists I guess
Yes, use Local Media Assets
See the article for shows for naming
Disclamer: Not tested 
since your use case is very special, but do try it out
If you want to organize your videos like a tv show with seasons and episodes, you must create a library of the type “TV Shows”.
Also your files must be organized and named as required for a tv show. Naming Home Series Media | Plex Support
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