Can you confirm that the app is running in task manager?
Can you share what is under your [ui] key from the player’s plex.ini file? Located here: "C:\Users\DragonStare\AppData\Local\Plex\plex.ini".
Can you share your logs in that same directory as above?
Lastly, close the player, then delete everything under [ui] key from the player’s plex.ini file and see if you can reproduce the issue.