Why is this so difficult?
What you should be doing is this:
Movies Library (whose Library type is: Movies) points to
..\[media]\Movies\
TV Shows Library (whose Library type is: TV Shows) points to
..\[media]\TV Shows\
Example of appropriate file location for a movie in said library:
..\[media]\Movies\3 Days to Kill (2014)\3 Days to Kill (2014).m4v
NOTE: Per the above example, put each movie in its own movie-specific-named subfolder that is in the Movies folder. The subfolder for that movie can then contain downloaded trailers, subtitle files, et al. for that movie and makes scanning/adding/changing files for that movie alone much easier on the Plex software.
For example:
..\[media]\Movies\3 Days to Kill (2014)\3 Days to Kill (2014).en.srt
..\[media]\Movies\3 Days to Kill (2014)\Theatrical Trailer-trailer.m4v
..\[media]\Movies\3 Days to Kill (2014)\Arbitrary Extras Name-behindthescenes.m4v
Example of appropriate file location for a TV Show episode in said library:
..\[media]\TV Shows\Stargate SG-1 (1997)\Season 1\Stargate SG-1 - 1x03 - The Enemy Within.m4v
Do NOT have Movie Libraries pointing to TV Show Library subfolders nor TV Show Libraries pointing to Movie Library subfolders. In the examples above, NO Library should be pointed directly at ..\[media]\ because it contains subfolders with both movies and tv shows, and thus will confuse Plex if a library is pointed there.
I repeat. Do NOT do this:
..\[media]\Movies\3 Days to Kill (2014)\3 Days to Kill (2014).m4v
..\[media]\Movies\TV Shows\Stargate SG-1 (1997)\Season 1\Stargate SG-1 - 1x03 - The Enemy Within.m4v
nor this:
..\[media]\TV Shows\Stargate SG-1 (1997)\Season 1\Stargate SG-1 - 1x03 - The Enemy Within.m4v
..\[media]\TV Shows\Movies\3 Days to Kill (2014)\3 Days to Kill (2014).m4v
nor any variant thereof.
If you have miniseries that are not technically TV Shows (like “John Adams”, “From Earth to the Moon” or “Roots”), they are still episodes of a series, and therefore should be in a library of the “TV Shows” type (you don’t have to call a tv-show-type-library “TV Shows”. The name is arbitrary.) The TV Shows library type organizes multiple episodes per show/series; the “Movies” library type organizes individual films with additional extras, trailers and featurettes.
Having a single film split across multiple discs (like Fellowship of the Ring, discs 1 and 2) is still a single film and should either be labelled correctly so that Plex combines both files into a single movie entry:
..\[media]\Movies\The Lord of the Rings- The Fellowship of the Ring (2001)\The Lord of the Rings- The Fellowship of the Ring (2001) - disc1.m4v
..\[media]\Movies\The Lord of the Rings- The Fellowship of the Ring (2001)\The Lord of the Rings- The Fellowship of the Ring (2001) - disc2.m4v
or else they should be muxed together into a single file using software like MKVtoolnix.
