Back when people still used dial-up, I once observed a sys admin in our IT department using a custom, proprietary Windows application developed by a vendor, used for ordering purposes. The whole thing was proprietary, client, protocol, and server, and it was awesome to behold.
That was pretty common back in those days. With the appification of a lot of websites, it’s coming back (albeit using rest instead of a proprietary protocol).
I have a windows vm that I use perhaps every few weeks for sketchup (because for the life of me, I cannot get wine to run it correctly -- it'll run but not SAVE...).
Every time I run the VM, it has windows updates to install. I guess it's a bit nicer swiping away from the VM and doing something else when it updates but it's a real solid reminder why I "moved away".
I've noticed there is a point in dual booting where you do enough in Linux that you can't get back to windows without it updating. This pushes you to stay longer and longer in Linux, to avoid the dreaded update.
I've already seen a few people accidentally pestering themselves out of windows this way.