Plex doesn’t have a concept of ‘Titles’. It only knows
- A movie can have chapters. Which means one, contiguous video file and ‘chapter markers’ embedded into it.
- A movie can also have Extras (videos) associated with it
You need to find out which approach is better for you.
Either you merge all your titles together, to get one large file with chapter marks
or
you pick one of the titles as the ‘main feature’ and add all the other titles as Extras.
Or perhaps a mixture of both approaches.
The tools to get either are
- makemkv
- MKVtoolnixGUI