Thanks for the screenshots and log. Unfortunately you have debug logging disabled on Plex Media Server
Please try again to get similar diagnostics with also the directory contents screenshots
I can see that it relates to comskip - so you could disable it until the issue is identified
May 21, 2019 22:13:51.278 [0x7f6bb53da700] ERROR - Couldn't rename file "/borg/media/videos/TV/.grab/62ea5fea20b2ddfd7323ce9fda10700cbe02216b/The Voice (2011) - S16E24 - Live Finale Part 2.ts" to "/borg/media/videos/TV/The Voice (2011)/Season 16/The Voice (2011) - S16E24 - Live Finale Part 2.ccyes/The Voice (2011) - S16E24 - Live Finale Part 2.ts": Not a directory
For logs - see
https://support.plex.tv/articles/201643703-reporting-issues-with-plex-media-server/
https://support.plex.tv/articles/200250417-plex-media-server-log-files/
