i think its fixed! thank you so much!
i actually kinda knew that i have the permissions messed up, i’m still catching on with the BSD perms. i just didn’t think that would be the issue for SSL. i simply gave the “plex” user full permissions for the entire directory, recursively
i connected securely for the first time from 2 different remote connections AND locally as well 
would you maybe check the fresh logs to verify that we fixed it permanently?
(File removed)
(all verbose logging finally turned off now)
thank you so much. if you ever find yourself in Croatia, give me a ring so i can treat you to a nice meal 