I agree with some of what you are saying (healthcare, educational arms race..) but you live in one of the most expensive areas in the US (the world?). That is a personal choice.
(also buying a car thats ~5 years old is much more cost efficient than buying new)
Well, it's sort of a personal choice. I was born and raised in metro-Boston, my family is here, my dad was born and raised here, etc, So when I'm comparing standards of living I am comparing against that of my family before me.
(also buying a car thats ~5 years old is much more cost efficient than buying new)