I did the math on this about 1.5 years ago and came to the conclusion that it wasn't worth it. I was, at the time, in a CTO-level position at a VC-funded startup and so had plenty of opportunities in the Bay, but in the end opted to live in a quiet country town about 2.5 hrs drive away and work from home in a lower-key role.
I have a 3yo kid and another on the way, and I do not regret my decision for one second, particularly when I hear horror stories from my stressed-out friends in SF/SJ. Also we can easily pay the mortgage on one salary and my wife is able to finish her PhD without us going into debt.
For us, it wasn't just about salary vs cost of living, but also about the stresses of big city life, competing for limited places in overtaxed childcare, sitting in traffic for hours every day, and being surrounded by other parents enduring the same tortures. No thanks.
This is open source. You can run it locally, host it yourself, put it on Heroku -- whatever your heart desires. And, yes, you can always just use WordPress.com (for free, btw). And that's just out of the box; The sky's the limit if you get involved as a contributor (and you should!)
Where does this leave WordPress.org? Well, let's put it this way: There will be a lot more people building cool things on top of the WordPress.org REST API now that this project has shown what can be done (I expect that over time the REST API will accumulate all the abilities of the Jetpack API)
Does there have to be a better strategy for WordPress.org? I don't fear for a project that has already claimed 25% of the web and is growing market share faster than any other CMS.
http://www.goldsounds.com/yoyo/