Thanks everyone for your ideas and tips.
I think it is as good as it gets for now.
Here is where I ended up overall. (Grade C)
My primary goal was to have a more user (wife) friendly place / way to find and view recorded content, instead of folders and file names and different apps for different recordings.
Everything is through Roku, other than live TV
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Migrated PLEX from my underpowered Synology Server (1512 (9 years?) old box no HW transcoding) to a 5 year old I7 Laptop with Nvidia
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Added a cheap used HD Homerun Box (without SiliconDust DVR Activation) just to enable Plex DVR
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I record non-broadcast shows (streaming sources) with Playon SW [highly recommend]
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I record a few OTA broadcast shows with HDHomeRun
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I created a plex library for TV shows that monitors both my Playon Server Directory (Local Laptop Drive) and my main NAS Media directory
As far as Plex commercial skip it is still hit or miss. I would estimate maybe 60% success, which seems way to low to me, but it is what it is.
Results
Playon Recordings - About 70% Success through Plex, seems to vary by streaming source.
Initial Testing, not complete, is that Hulu Sources seem to skip fine, and Peacock has built in chapter markers for commercial skip, but 80% of the time Plex does not skip commercials from Peacock, I can press down on the remote and just move to the next chapter, so that is an OK work around. BTW native commercial skip from Playon Roku App is 99% effective. But keep in mind my goal is a single interface (one app)
HDHomeRun Recordings - No real pattern, some shows it works others it does not, no pattern that I can determine between shows, networks, etc. I would estimate this is about 50-60% effective. Even within the same show sometimes it works at first then as the show continues it stops working. Again, I can record the same show via Playon and it is 99% effective, so here I can clearly say that Plex Commercial Skip could use some improvement.
As far as Settings,
Currently I have “find chapters” and “create thumbnails” turned on to try to force Plex to rescan files. I have scheduled tasks running 23 hours a day 00-23, but I rarely see any activity in the dashboard. I have use HW Transcoding enabled. As time permits I’ll take a closer look at the logs. I don’t have a massive amount of content, maybe 1000 episodes [is that large?], but it does not seem to be spending enough time analyzing the files. So I wonder it if is hitting a file or condition, then stops the scan.
I have scans set for hourly, and “when media is added”.
On the Plex Roku App, I have experimented with all the setting there to try to force Plex to transcode on the fly to see if that improved anything (no change)
As I said, I have enough functionality where the convenience of having all my media in one place with proper descriptions and resume where you left off, to make it worthwhile. Once I have tumbnails generated for fast forward it will help a lot when skip is not working. Overall I rate my setup as “C” but that is up from a “D” with having to browse folders to manually launch a show.
Thanks Plex, Thanks Forum.