While it's true about the schools, I don't agree with you on your other points. It seems like PG is cognizant of change around and within him.

It wasn't by pure luck that he started Ycom, and it wasn't pure luck he started Viaweb. With viaweb he had a first mover advantage sure, but had already noticed tech and programming were interesting and changing the world. Ycom, as he said, angel investors didn't exist before Ycom. He almost created the term. Hardly luck.

It's certainly true the moving around schools, the cheap apartments etc is just not possible today.