A few years ago, I bought a 3-bedroom house in East Bay area, with a nice backyard (which looks distinctly less nice now, but hey, programming is a time-consuming job), and a decent public high school in walking distance for my two kids, all the while getting a whooping <$250K salary. Still had enough money left to invest in mutual funds and enjoy trips to Hawaii every other year or so.

I honestly don't know what to say. If you really think 300K/year is barely livable then I hope someone in your family has a sit down with you and ask blunt questions about what the fuck you're doing with all that money.