Hi enklaris and welcome to Apple Support Communities.
I see you are having some difficulties in using a USB hub and it sounds like the issue came to a head after a macOS update.
First, I'd like to have you do an SMC reset. The following article goes over the steps:
How to reset the System Management Controller (SMC) on your Mac
Are you using one of the adapters/docks officially sold by Apple such as those here?
https://www.apple.com/shop/mac/mac-accessories/power-cables?page=1#!&f=adapter-dock&fh=4595%2B45e3%2B45b0
If you're using a different adapter, the issue may be with its internal driver not being compatible with the latest update. I'd advise trying it on a different Mac to isolate and make sure the dock itself has not failed. If it works on a different device running a different OS, then you'll want to reach out to the company that made the dock for options.
Cheers.