Actually there are various ways to get proper matches without the exact filenaming convention they recommend. There's a feature where you can "Fix Incorrect Match" described here:

https://support.plex.tv/hc/en-us/articles/201018497-Fix-Inco...

This lets you pick the movie/show/whatever manually from a few different sources. If your media isn't immediately recognized, you can do this to correct it.

Additionally, they have a "Personal Media" metadata agent you can select for media that's your own personal media (like home videos) which will allow plex to read the metadata directly from the file instead of searching for a match. There's more info on that here:

https://support.plex.tv/hc/en-us/articles/200265246

I have never had the issue you described where something doesn't show up at all, just that it's incorrectly matched (in which case the tile will just show a screenshot and the title will just be the filename)

Additionally, I've found that if you use their recommended folder structure, the filenames matter much less. For example, if you have this directory:

/Media/TV Shows/Show Name/Season 1/

It seems like as long as the file contains the season/episode like "S01E01" it will match correctly based on the directory information. I haven't messed with it much but I have never had to rename a file to get plex to recognize it when I use directories like this

user:	ishields
created:	November 23, 2016
karma:	91