Need some help fixing duplicate/mismatched files

AFAIK, ~ & similar characters are OK.

What I was trying to say (albeit not very clearly), was that if you add /TV Shows to your Plex TV Show library, then you cannot have subfolders such as ~Documentaries underneath.

However, it is certainly OK to add ~Documentaries to a TV Show library, as it is the folder containing the TV show files.

Examples:

Not supported:

/TV Shows  <-- Folder added to Plex Library
.../~Documentaries  <-- Not supported
....../Planet Earth

Supported:

/TV Shows 
.../~Documentaries <-- Folder added to Plex Library
....../Planet Earth
/TV Shows  <-- Folder added to Plex Library
....../Planet Earth

Another thread along similar lines: