Every time I think about my Windows installation I think about AHK and get a little sad. It's the only software I regret leaving. But then I remember my comfy i3 config, and get over it.
I think you should think about moving to more FOSS-friendly OSes, but in time, down the line, not this instant. Maybe the next devices you'll own, or when you feel ready, comfortable, with privacy; anyway, GL!
I'd start small, a lot of people would tell you to do some drastic changes to you life, but, like every other thing you have in life, start small, or you'll might fail.
You could use Shelter for secondary 'profile' (user).