@Pleitao - I had a quick look at your log and it looks similar to mine specifically this line:
2021/08/06 01:06:34.192 (238 MB) (15078) ❌ PMPrePlayHeaderViewModel.m:937 | Error requesting immediate download for item <PMKMetadata:0x132fd9d60 key:/library/metadata/90071 title:N Is for Night Terrors type:4 isDirectory:0>: Error Domain=PMKHTTPResponseError Code=404 "Response error" UserInfo={NSLocalizedDescription=Response error}
I can make some guesses at what it means, but hopefully this points a Plex dev in the right direction.
A minor observation, in your log there are 172.16.** IP addresses mentioned, this makes me think you are probably running your Plex server inside Docker? I am also. I have not tried outside of Docker, but of the strange issues I have had with Plex in the past, they tended to end up being network and/or Docker related (most memorable was the DNS Rebind bug that stopped Direct Play from working).
