Try adjusting your naming convention to something that is series/episode based…
also I would advise using the Plex Media Scanner rather than the ASS if you are using that.
:.
└───GameGrumps [UC9CuvdOVfMPvKCiwdGKL3cQ]
│ s01e001 - Bloodborne - Come at Me, Beast! - PART 1 - Game Grumps [g0dJ-NhPR2A].mkv
│
├───Bloodborne OLD
│ s02e001 - Bloodborne - Come at Me, Beast! - PART 1 - Game Grumps [g0dJ-NhPR2A].mkv
│ s02e002 - Bloodborne - The Purge - PART 2 - Game Grumps [_6jh-rY7--U].mkv
│ s02e003 - Bloodborne - Turning Heads - PART 3 - Game Grumps [JBvEBPiMshc].mkv
│ s02e004 - Bloodborne - Death Barf - PART 4 - Game Grumps [RpBdel8Btgs].mkv
│ s02e005 - Bloodborne - Date With Death - PART 5 - Game Grumps [_r11R5JK1j8].mkv
│ s02e006 - Bloodborne - To Fight or Not to Fight - PART 6 - Game Grumps [NTCPH4VbUq4].f137.mp4.part
│
└───Bloodborne [PLRQGRBgN_EnqGHZ_4ZVWBj1MTfpDQeU-N]
s03e001 - Bloodborne - Come at Me, Beast! - PART 1 - Game Grumps [g0dJ-NhPR2A].mkv
s03e002 - Bloodborne - The Purge - PART 2 - Game Grumps [_6jh-rY7--U].mkv
s03e003 - Bloodborne - Turning Heads - PART 3 - Game Grumps [JBvEBPiMshc].mkv
s03e004 - Bloodborne - Death Barf - PART 4 - Game Grumps [RpBdel8Btgs].mkv
s03e005 - Bloodborne - Date With Death - PART 5 - Game Grumps [_r11R5JK1j8].mkv
s03e006 - Bloodborne - To Fight or Not to Fight - PART 6 - Game Grumps [NTCPH4VbUq4].mkv
s03e 007 - Bloodborne - CHARGE....NOT CHARGE - PART 7 - Game Grumps [cXTnzkc5ND4].mkv
s03e008 - Bloodborne - Smash the Pots! - PART 8 - Game Grumps [YZqQWvRkH1I].f137.mp4
