"Dual-boot is unsupported by both Windows and Ubuntu"... what? I have dual-booted almost every machine I've ever owned, including my Mac boxes. It is one of the standard options offered during installation. How does that "break lots of assumptions"?
I have the expertise to get around the various roadblocks (features?) but it costs a lot of very unproductive time. I skipped over the saga of trying to get WSL2 working, another source of frustration and loss of time.
I also left out the part that Windows will force updates unless you pay for their upgraded version. When I develop code I have a lot of "state" in open windows, an editor, browser tabs, and test runs. Microsoft just decides that the machine is "idle" and decides to reboot it, losing my work. Is it an "unrealistic assumption" that my work is of some value to me?