MacOS Plex Server Crashing

There are crashes during scheduled tasks

At these times
Sep 25, 2023 14:59
Sep 25, 2023 19:34
Sep 25, 2023 21:08
Sep 25, 2023 21:14

Can you tell me what do you have specified in server settings for the Transcoder Temp Directory ? You can see the value in server advanced settings for the Transcoder
and also in terminal - by executing this command

defaults read com.plexapp.plexmediaserver  TranscoderTempDirectory

The crashes appear to be whilst trying to create a temporary transcoding folder within that path

and if there is a valid absolute path specified, could you check the ownership and permissions

Update 1 :
Also noticed this file not found error

Sep 25, 2023 21:14:25.945 [0x1e0e76080] ERROR - Exception analyzing media file '/Volumes/media/Italia/Fratelli di Crozza/Fratelli.Di.Crozza.S14E01.1080p.WEB-DL.AAC2.0.H.264.mkv' (Could not parse /Volumes/media/Italia/Fratelli di Crozza/Fratelli.Di.Crozza.S14E01.1080p.WEB-DL.AAC2.0.H.264.mkv (error=-2): No such file or directory)

Are the discs attached / mounted correctly ?
Could be similar issue with the transcoder temp directory path

Update 2:

Have you copied the Plex Media Server database from a windows setup ?
I noticed this in one of the logs

Sep 25, 2023 19:13:41.554 [0x1e0e76080] DEBUG -   * Scanning Z:\Calibration
Sep 25, 2023 19:13:41.554 [0x1e0e76080] DEBUG -   * Marking media not available in Z:\Calibration

May be your transcoder temp directory path is a windows drive path !!