You should stop listening to whoever told you Debian is hard to set up or keep running immediately, and never go to them for advice, ever again, about anything.
If you can install Plex on Windows, U until, or MacOS you can install it on Debian. It’s not fucking Arch ffs.
I read your entire post. You sound like you want to use either Ubuntu or Pop. If you want to use them, use them.
Why ask for recommendations if you’re just going to say “Thanks but no thanks”?
Being a dick would be attacking you directly, which I’m not doing. Being a dick would be asking a question that looks a lot like bait, then passive aggressively shooting down everyone that gives the answer that 99% of people will give to the bait question.
;)