@Elijah_Baley :
Because you are not alone in the wild. Maybe there are multiple solutions out there that are used concurrently. Maybe a different software is doing some auto-naming, maybe it is just hard for people to rename hundreds or thousands of files and folders (even with tools). Maybe people want software to be flexible, not software wanting people to be flexible. Maybe they don’t like the rules because of different approaches to this. snip hundreds of other reasons snip
What makes me really sad: You are blatantly CLAIMING that it is the naming scheme. You are not trying to find out why things sometimes work and other times don’t. This is really not the way it should be. “Go and do it my way or leave me alone” is what you are really constantly telling people.
In my case, it is “Die Hard 4” (or whatever its English title really is) that gets a duplicate whenever I forget to change the file name of a random other movie with a complete other PATH containing a complete different title and year and that file name contains a 4 and looks similar to that used in Die Hard 4. It is not that I get an easy notice of that because it is just GONE (as in the scenario of the poor other guy). I have to search for duplicates to even notice my “failure to behave correctly”. If I just delete the “4” in the file name and Plex dance with it, then it is correctly identified.
Maybe if you invest some time and effort, you would find out that the software can be amended to get even better than it is.
Maybe you can LEARN something from them… HOW they are naming things and WHY they are naming them that way and get the software to take care of that instead of getting people to work the software’s way.
Tell my wife that she should use a tool to rename files… man, she would not even know what you are talking about and she would love at you for making such ridiculous, tech-fancy suggestions. She would just ask: “Why does your software not properly interprete this?” … My wife is not stupid, she simply does not want to invest any more time than necessary in this. And it is generally a good idea to think twice about what my wife is telling you and then just say “yes, madam” and do it… 
If you would obey my wife’s way of thinking, you would definitely have a better solution to this (probably a mechanism footprinting the movie itself and magically identifying them whatever they are named). Greetings from her… really, she is sitting next to me, having much fun.
BTW: “What I always fail to understand is the resistance to following the guidelines.”
… is something I do not ever want to hear from anyone who is selling software or helping others in doing so.
Cheers
