My Movies share is kind of an historical mess.
It BOTH has several movie files (and all of their corresponding .nfo and description files) but ALSO separate directories under it for other movies.
In that case of course each directory has a single movie and also the .nfo etc in it.
In this case when I define a Movie repository in OSMC, in the “Content scanning options” should I flag the “Movies are in seperate folders” or not?
The other “Scan recursively” is selected and active.
Scan recursively is probably the best choice. If you select “Movies in separate folders” I don’t think Kodi will find the movies not in folders. It’s best to pick one method of storage and stick with it, but I think the recursive scan will catch everything.
Figured out by trial and error that in my case it seems best to flag them both.
Kodi’s wiki covers the explanation of these settings. Movies in folders is regarding where it decides to discover the content matching from, not where it is looking for files to match for.