Plex and Mojave issues

Great thanks. It’s a little roundabout trying to find that “More” menu, but it’s the best menu because it operates on the all libraries, and it’s the only place you’ll find the Empty Trash

The steps I listed above are called The Plex Dance. It’s how you get Plex to scan items again from scratch like it never saw them.

I’ll have a look at the logs.

EDIT:

Okay so it looks like database corruption errors from SQLITE3 that fill your log.
Click the triangle to expand the list.

in "Plex Media Server.log"
Sep 22, 2019 09:16:40.162 [0x7000008e9000] DEBUG - Updating metadata item (save) (original2.MOV00234) with ID 6198186
Sep 22, 2019 09:16:40.177 [0x7000008e9000] ERROR - SQLITE3:0x10d29afb0, 11, database corruption at line 79051 of [bf8c1b2b7a]
Sep 22, 2019 09:16:40.177 [0x7000008e9000] ERROR - SQLITE3:0x10d29afb0, 11, statement aborts at 11: [SELECT idx, start_block, leaves_end_block, end_block, root FROM 'main'.'fts4_metadata_titles_segdir' WHERE level = ? ORDER BY idx ASC] database disk image is malformed
Sep 22, 2019 09:16:40.177 [0x7000008e9000] ERROR - Failed to commit transaction (../Library/MetadataItem.cpp:961) (tries=1): Cannot commit transaction. database disk image is malformed
Sep 22, 2019 09:16:40.608 [0x7000008e9000] ERROR - SQLITE3:0x10d29afb0, 1, statement aborts at 1: [COMMIT] cannot commit - no transaction is active
Sep 22, 2019 09:16:40.609 [0x7000008e9000] ERROR - Failed to commit transaction (../Library/MetadataItem.cpp:961) (tries=2): Cannot commit transaction. cannot commit - no transaction is active
Sep 22, 2019 09:16:41.471 [0x7000008e9000] ERROR - SQLITE3:0x10d29afb0, 1, statement aborts at 1: [COMMIT] cannot commit - no transaction is active

Sep 22, 2019 09:16:46.291 [0x7000008e9000] ERROR - SQLITE3:0x10d29afb0, 1, statement aborts at 1: [ROLLBACK] cannot rollback - no transaction is active
Sep 22, 2019 09:16:46.291 [0x7000008e9000] ERROR - Failed to roll back transaction (../Library/MetadataItem.cpp:959): Cannot rollback transaction. cannot rollback - no transaction is active
Sep 22, 2019 09:16:46.291 [0x7000008e9000] ERROR - Exception analyzing media file '/Users/jayrobinson/Pictures/iPhoto Library.photolibrary/Masters/2004/Photos Clubbing/original2.MOV00234.MPG' (Cannot commit transaction. cannot commit - no transaction is active)
Sep 22, 2019 09:16:46.320 [0x7000008e9000] ERROR - SQLITE3:0x10d29afb0, 11, database corruption at line 79051 of [bf8c1b2b7a]

Sep 22, 2019 09:16:52.398 [0x7000008e9000] ERROR - SQLITE3:0x10d29afb0, 1, statement aborts at 1: [COMMIT] cannot commit - no transaction is active
Sep 22, 2019 09:16:52.398 [0x7000008e9000] ERROR - Failed to commit transaction (../Library/MetadataItem.cpp:961) (tries=10): Cannot commit transaction. cannot commit - no transaction is active
Sep 22, 2019 09:16:52.398 [0x7000008e9000] ERROR - Exception inside transaction (inside=1) (../Library/MetadataItem.cpp:961): Cannot commit transaction. cannot commit - no transaction is active
Sep 22, 2019 09:16:52.398 [0x7000008e9000] ERROR - SQLITE3:0x10d29afb0, 1, statement aborts at 1: [ROLLBACK] cannot rollback - no transaction is active
Sep 22, 2019 09:16:52.398 [0x7000008e9000] ERROR - Failed to roll back transaction (../Library/MetadataItem.cpp:959): Cannot rollback transaction. cannot rollback - no transaction is active
Sep 22, 2019 09:16:52.399 [0x7000008e9000] ERROR - Thread: Uncaught exception running async task which was spawned by thread 0x700000348000: Cannot commit transaction. cannot commit - no transaction is active
Sep 22, 2019 09:16:52.411 [0x700000f0d000] ERROR - SQLITE3:0x10d29afb0, 11, database corruption at line 79051 of [bf8c1b2b7a]
Sep 22, 2019 09:16:52.411 [0x700000f0d000] ERROR - SQLITE3:0x10d29afb0, 11, statement aborts at 11: [SELECT idx, start_block, leaves_end_block, end_block, root FROM 'main'.'fts4_metadata_titles_segdir' WHERE level = ? ORDER BY idx ASC] database disk image is malformed
Sep 22, 2019 09:16:52.411 [0x700000f0d000] ERROR - Failed to commit transaction (../Library/MetadataItemClustering.cpp:114) (tries=1): Cannot commit transaction. database disk image is malformed

You next goal is to follow the steps listed in Repair A Corrupt Database.
It’s reasonably safe because you’ll be repairing a copy of the current DB,
then moving that into place later in the steps.

Let us know how it goes.