How do I manually add trailers to Plex 2018?

not exactly sure which guide you’re referring to.
it appears you’re talking about 2 separate features…

1. Local Media Assets -> Trailers

With Local Media Assets enabled in the agent used for your library, Plex will look for those files on your library/movie folder. It’ll be important to follow Plex’ naming conventions:
https://support.plex.tv/articles/200220677-local-media-assets-movies/

Examples:

  • Movies > Rogue One - A Star Wars Story (2016) > Trailers > Theatrical Trailer.ext <- identified as trailer by parent folder
  • Movies > Rogue One - A Star Wars Story (2016) > Theatrical Trailer-trailer.ext <- identified as trailer by the filename suffix
  • Movies > Rogue One - A Star Wars Story (2016)-trailer.ext <- if you’re not using separate folders for each movie and Plex finds this file next to the actual movie file with the same name

Playing Cinematic Trailers before watching a movie

This can be activated in your library’s advanced settings (Play Cinematic Trailers). Without a Plex Pass, this will check the pool of trailers available in your own library (not necessarily the trailer of the movie you’re about to watch.

for more you can check out this support articles: