Thanks that was a great analysis. Once you started in I did recall about half those details, but mostly I guess it needs to go on my reread pile since I've forgotten so much.
As a tangentially related side - one of the first emails I ever sent when I first started to use email in about 1996 was to Anne McCaffrey.
I was in the "everything you can imagine is on the internet" phase of just looking up random things, and somehow I found her email address.
I sent her a short note about how much I'd loved her books, and she sent me a brief, nice note back.
That email is long lost to the twists and turns of life - I didn't even understand the concept of keeping backups back then (Edit - that's not true, it would be more accurate to say I just never bothered) - but it was a cool little interaction that I always remember fondly. 🙂
Unless you have very specialized requirements (and quite possibly you do) the solution is usually to unhook yourself from thinking of needing specific programs and to instead focus on needing to perform specific tasks. (Then finding the Linux way to perform that task.)
Barring that, the codeweavers suggestion is a good one. I used it in my early days when I thought I couldn't live without particular pieces of Windows software and although that was several years ago, even then it was pretty good about being able to easily run arbitrary Windows software. IMO it's cheap enough to be worth the investment.
If you truly have bespoke requirements that just can't be satisfied by either of the above, staying on Windows may legitimately be your best option.
More generally - if you decide to take this step, expect to have to learn to use a computer substantially differently than you have in the past. It's not harder; in many ways it's easier. But if you are very experienced and comfortable with Windows, a lot of concepts are going to feel foreign to you. Tackle one task at a time and your experiences will build upon each other. Go into it expecting to have to learn, and you'll do fine. Bizarrely I find the least tech-savvy folks sometimes have the easiest time transitioning.
Yep that would be just the picture to post about an information freedom activist driven to death by the US justice system. that's why it says "Aaron Swartz day" in OP, because it's a pic of Rishi Sunak.