It all depends on whether you want to be able to pick any of the individual songs and play them solo.
Or whether you want to treat the videos more like a real concert so it plays continuously.
You can’t have both (for now, at least).
Give up the division into 2 discs. It is not necessary and does more bad than good.
Option one:
pick any of the individual ‘Song’ files and name it like it is the main item. Or you pick a sort of intro video or an interview which might be included on the discs.
Concerts /
Pink Floyd - Pulse (2006) /
Pink Floyd - Pulse (2006).mkv
Then take all of the other songs and rename them to their song titles. Then create a subfolder and name it Scenes. Put all of the songs into it.
You may want to make another subfolder Behind The Scenes and put all the video bonus material from the discs into it.
Concerts /
Pink Floyd - Pulse (2006) /
Pink Floyd - Pulse (2006).mkv
poster.jpg
Scenes /
Shine On You Crazy Diamond.mkv
High Hopes.mkv
Dark Side Of The Moon.kmv
...
The result might look similar to this, but only if any of the online movie databases “knows” this concert. If they don’t know it, you must “match” it to ‘Personal Media’ and put in a textual description and a poster image yourself. You can also put a poster.jpg besides the video files as indicated above.
Second Option:
Either rip the discs again or merge the individual song files to be one big file.
Bonus point of the re-ripping option: you may get chapters from the disc which you can edit to contain the real song titles (again with MKVtoolnix).
(right now there is only real chapter support in the iOS client, but the rest of the official Plex clients will get them too, eventually)
The rest can be obtained from this post which I did earlier:
https://forums.plex.tv/t/so-how-do-you-all-handle-concert-videos/133621/3
All of the above is following the rules for ‘Local Extras’ for movies. So the library must be a movie library and the ‘Local Media Assets’ agent must be active for it.
