There is no guide that I know of, and in addition sometime the actual contents of the log files will gradually change over time with new Plex server versions so you have to be open to the possibility that a log search term that was previously very useful MIGHT no longer appear.
Plex logs are most useful if you have debug level logging enabled and verbose level logging disabled. Verbose is simply too much logging and causes the logs to roll off too quickly in most cases. This guide provides the same guidance.
Inside the log zip that downloads the most valuable logs to start with is almost always the “Plex Media Server.log” series of files. “Plex Media Server.log” is the log that is currently being written, “Plex Media Server.1.log” is the next most recent, etc. If the issue happened before “Plex Media Server.5.log” then it’s been too long and you will have to wait for the problem to happen again and download logs more quickly after the issue.
Start looking for the string “ERROR” in the logs. If you have a Linux computer available then grep for all lines with “ERROR” can be a good way to start. Not every instance of “ERROR” indicates an actual problem, so you have to read and interpret to see if the error is associated with your particular problem. If Plex has simply chosen not to record a particular episode, as opposed to getting an error when it tries to record, it will normally NOT show as an error and you have to wade through the scheduling decision making in the logs to see if you can find why it decided not to record that episode.
Typically if Plex tries to record and receives an error then in Plex Web → Live TV → DVR Schedule it will show the recording attempt with a graphic of an exclamation point, but I’ve seen cases that it doesn’t.
In the advanced recording options for this show, do you have “Keep” set to anything other that “All Episodes”? About 6 months ago there was a bug that was causing the automated deletion process to delete the episode immediately after the recording finished if this was set to keep based on date. I thought this had been fixed, but…
Hope this helps.