If the problem is no output at all, it may be just a matter of toggling some HDA codec GPIO or EAPD pin to power up external amplifier chip, which can be done with hda-analyzer. But if it's some combo headphone/mic jack and detection doesn't work then I have no idea.

As headphones yes but good luck using the mic.

Another gem from this fresh windows install - headphones will work only if I boot into Windows while headphones are plugged in. If I boot without headphones and then plug headphones after I log in - no sound in headphones :)

My point is - there are all kinds of bugs in all popular OSes. I bet MacOS have bunch of them too. You just getting used to ones. Like it is never a problem for me to fix a webcam in linux, but it frustrates me to download 600 megs of drivers software to get my video card functional. The same way OP really frustrated by broken webcam and not really concerned about windows needs to update drivers, constantly monitor for viruses, etc.

One thing I noted tho - most frustration with Ubuntu (or any really linux desktop) I see comes the fact that some particular hardware is not working. The same hardware often have problems on Windows platform. And more often than not drivers/software for this hardware are closed source with bugs which never get fixed (because manufacturer's business in selling hardware, not software.) So apparently we would not have most of these issues with any OS if software required to run hardware would be open sourced. This will never happen probably tho..

I can assure you that I didn't have this issue in Linux. :) There were other issues, of course, but they were at least solvable.

1. I have an external USB microphone. Works fine (most of the time, see below), except it's always a default device for both input and output. I don't understand why. I expect my extrnal speakers to be the output source if nothing else is plugged in. I have to often manually change the output source.

2. Sometimes I want to use headphones. And sometimes when I plug them in, the output doesn't switch to the headphones. So I have to do it manually. Occasionally it still doesn't work and the sound continues playing through the speakers.

3. Happened to me a few times - my USB microphone disappears completely from the device list. Even though the light is on. Unplugging and replugging doesn't work either; only a complete reboot does.

I even have a custom bash command that restarts pulseaudio. I'm using it more often than I should.

Headset does not work on Windows: “This is crap, I’ll tell everybody I know to stay away from these headphones!”

I actually had the opposite situation with Ubuntu 20.04 on my desktop, got a lot less noise from my mic port under Ubuntu for some reason.

Using the 3.5mm output jack of the computer into a bluetooth transmitter works much better for me. 3.5mm does the one thing it should do, transmit the audio signal, without all kinds of unwanted software side effects, the PC has no clue what I do with my headphones and given the bugs mentioned above that's a good thing.

I wonder what's wrong with my system to have such bad USB audio experience :/

After I finish this next course I will try again with a different distro, and then see if my other USB mic that worked on the Chromebook (running native Linux) also works on my main machine.