You make a good case. In my more simple case, I need efficient and smart looking PowerPoints and no foss alternative can beat office 2016. And dozens of programs are windows only. I’ve tinkered with wine/play on Linux before and it just doesn’t work out of the box for the majority of programs.
My most recent example with EndeavorOS was trying out KDE which I thought looked really smart on the desktop. Then it started glitching. Arch tends to be bleeding edge so that makes sense. But it meant I had to make a new choice of distribution or DE.
But Debian based Ubuntu? On Virtualbox? That seems a bit off. Maybe LTS would provide the stability you need.
I guess because development is decentralised, that you end up with developers working on different packages and when they update one it has a ripple effect on other packages.