Thank you!

Previously I thought stock options were improbable to pay off.  After doing all the research for this guide I updated towards stock options being even more risky. My intention in writing this guide wasn't to prove stock options are worthless, but I see a lot of readers making this conclusion, and I understand why. As you said, it's a minefield of technicalities.

My softer personal takeaways:

1. Never expect to get rich via stock options, no matter if you think the company will go to the moon or not.
2. Early in your career, up to and maybe including Senior dev roles, stock options are just not worth it. You get little equity, so no big win even if all goes well, and zero ability to affect the outcome. You will get way more income by taking as much cash as possible and investing it properly. Absolutely work for start-ups, but for other reasons: experience, good people, connections, flexibility, etc.
3. Treat stock options of anything before series A as lottery tickets. After series A it's a proper business and the probabilities are much nicer.
4. To make the best of stock options you need to be senior in your career, at least a lead, preferably VP. Then you get more equity, so bigger upside, and you can do something meaningful to affect the outcome. 
5. You are in the best position if you can exercise stock options and pay tax on that without making a big dent in your budget. Because if you have the money you can exercise your stock options before an exit and see if it pays off, just treating that as a high-risk bet without compromising your financial goals. If you don't have spare money to exercise the stock options then it's insane to play this game. Apparently, you have much better chances of becoming rich from stock options if you are already rich.