I rebooted modem, router (which does have local cache but reboot clears it) and cleared caches in Plex on Synology per instructions. No change …
But … in trying to help another person in the forums about file names and resolving to agents I had a thought about a setting I know isn’t turned on and… “prefer local metadata” was enabled for my Library. I do not know if a recent update flipped that or I somehow triggered a change myself, but… that was the problem. I turned that off, did Plex dance, and it pulled the movie data correctly and applied the poster\background. I honestly have NO idea how that setting got swapped but there it is… 
I’m familiar with DNS but not clear why that URL (ocsp.digitcert.com) is resolving to my public IP address (24.207.223.209 is my Public IP) in NextDNS logs when TraceRT\Hostname lookup show [72.21.91.29] … but NextDNS does know my public IP so maybe something there is triggering a funny lookup result or is that actually right for that particular function happening there?
I don’t know if the failed resolve of ocsp.digicert and failed connect to server via my public IP are related but if DNS is resolving those together and If that’s not right I’d like to get it resolved … so any insight on those particular errors would be appreciated.
Special Characters - I may try a search/replace on those characters but I’ll probably just put it in a dedicated spot outside of Plex for now to avoid weird scans on it and preserve the data dump (originally part of an iPhoto library - which doesn’t play well with anything but AppleTV which I don’t have).
Thanks for your help! Sorry it was just a setting on my end but I appreciate the advice you gave based on what you saw in my logs.
