I think part of the problem is I have decades invested in proprietary software in the Windows ecosystem. If I didn't have that investment it would likely be easier. Don't make my mistake! :)

This is a sunk cost that in a few years will have been mitigated. You already understand the value proposition for Linux, otherwise you wouldn't have attempted this transition multiple times. So I think it's a matter of getting used to it.

But I also think context matters. Maybe you also need work that motivates you to use Linux or is impossible or quite inconvenient to do on Windows.

In any case, using Windows is fine. I don't think the user is to blame for the shortcomings of the brand. It's like with conscious consuming products that don't harm the environment. It's important to seek those, but if you have to go out of your way it's just not gonna happen.