Updates make using Windows 10 as an occasional dual boot on a laptop a pain. I usually use the machine with limited or no internet and no power handy, so if I accidentally let it update I'm SOL. As a result I found myself reaching for Windows less and less.

Do you need to dual boot? I switched to using Linux full time, and running Windows in a VM when needed. It also simplifies the workflows because you don't need to reboot to switch between the systems

If you're running Windows to play games, you need your virtualized Windows to be able to take 100% control (or close to 100%, anyway) of the GPU to get equivalent performance to playing the same game on Windows running directly on the hardware. This "GPU passthrough" turns out to be complicated to do, particularly on VirtualBox, which ('cuz it's free) is the virtualization platform your average hobby user is likely to be using.

(Which is too bad, because I would love to be able to stop dual booting just to be able to play some games.)

Now there is Proton by Valve. it's a wrapper for wine and a few other components. Most games just work now. There are of course some exceptions like ring of elysium doing kernel patches for ring zero DRM and Anti-Cheat. But I would say 90% of my steam library just works out of the box.

https://github.com/ValveSoftware/Proton/