This started when I attempted to push in a stick upside down.
Was it the stick that works sometimes and not others?
There was a short indeed due to the Windows message. Since you said other USB thumb drives still work I'm assuming the problem lies in the thumb drive its self.
There
might not be damage to the USB bus and what not after all. I need to be there to see exactly what's going on. Your top connector there looks like the header connector. But your computer looks OEM and doesn't appear you can simply disconnect USB ports without snipping wire. I would refrain from doing any of that if other USB thumb drives work.
There are two ports. It's the other undamaged one that wont accept the dodgy stick.
Now this leads me to believe there IS USB bus issues.
It's very hard for me to say because I literally need to be there and look at the computer.
It could all very well be some kind of driver mess up due to the temporally short that took place as well. You could try and run USBDeview, uninstall all devices and reboot. Be careful because if your mouse and keyboard are USB it'll uninstall those as well. Though, a PC reboot should reinstall those drivers. If you chose to run this utility, I'd first create a system restore point.
View any installed/connected USB device on your system
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PS:
You might want to refrain from even using USB sticks if there is USB bus issues. I'm thinking perhaps some, but not all USB thumb drives have internal protections and some don't so if your computer's front USB headers are messed up, it
could mess up other USB thumb drives. This I'm not too sure about, but it's something I need to research to see if certain USB thumb drive manufactures have protections in place and what those protections represent and how they work. Busy at the moment so it's on the back burner.
So, I just want to be clear.
The damaged USB port works? The undamaged USB port does not?
This is true for only one USB thumb drive? The Kingston 64 GB thumb drive? Other USB thumb drives work in both ports without issue?