That is most likely going to generate less revenue than promoting donations, or a comparable amount at best. WinRAR is the meme example.
From a PR and marketing perspective, if I wanted to maximize my revenue as a single developer I would set up a Patreon or encourage recurring donations through the software by providing bragging rights stuff (merch, insider access, early access to unfinished builds and so on). Single mandatory payments simply reproduce the piracy/license access of commercial software and shaming people into paying without coercion just makes you seem less appealing to people who would donate anyway.
Man, I’ve had two separate devices fail to install updates the last week, leading to tons of weirdness and troubleshooting. I even had to chkdsk c: /F at one point like a neanderthal.
I have enough coomputers laying around that I’d move more of them to other OSs, Linux included if I hadn’t tried that and found it as much or more of a hassle in those specific machines, be it compatibility issues or just fitness for the application. I’m not married to Windows at all, but there are definitely things that are much easier to handle there, which does justify sticking with it through the reinstalls and awkward weirdness on those.