Hi Joe,
Welcome to Microsoft Community.
It seems like you're facing a persistent issue where your Surface Pro 9 detects an external display but can't activate it. Since you've already tried many troubleshooting steps, let’s explore some additional solutions:
First of all, can you tell me what the resolution and refresh rate of your external monitors are? Please make sure they are not more than 3840 x 2160 60Hz. In addition, when you connect these two external monitors separately, can they display normally? You can try to swap the order of the first external monitor that was able to display normally before and the second external monitor that cannot display, and connect them one by one to see if the problem still occurs.
With your help and more detailed information, we can work together to find a specific direction to resolve your current situation.
Your Sincerely
Hahn. W - MSFT | Microsoft Community Support Specialist