As a married person with children now, having roommates is absolutely out of the question. I know people suggest it as a "solution" to the housing crisis but in no way is it acceptable in my mind to have strangers living in the house with my wife and children.
People making different choices than you aren't "living in squalor." You're going to have a hard time convincing me that a luxury apartment with separate bedrooms is squalor.
If someone really wants to emulate your lifestyle, they would be best served working in SFBA for the first 5-10 years of their career, so as to build out their resume. Once you're more established and have an impressive resume, it's so much easier to find lucrative remote gigs.
...oh wait, you mean $1000/month PER PERSON? Ha, no. In Kansas, you can pay $1000/month to own that whole house.
That would fall squarely in the 'living in relative squalor' category. making 200-300K and living with roomates in a small place? Pretty atypical for most of the world, and completely discounts most people over ~25 years old.
I can't speak towards family living, but as a single person willing to live with roommates, you can find pretty nice places in the heart of Silicon Valley for ~$1000/month. Now add in compensation-packages well over 6 figures, brand-name companies for your resume, networking locally with other great engineers/techies, and the ability to switch companies every 1-2 years if you're unhappy. I wouldn't ever recommend a 30-year-old giving up all that to work in Kansas.