As for the NY/250K issue, I would say that yes, a 250K household income in Manhattan doesn't allow you to be well off in quite the same way that it allows you to be well off in most of the rest of the country. The main issue is not only is real estate generally hideously expensive, but there's also a tremendous premium for anything bigger than a 2 bedroom apartment because there aren't all that many of them.
But you don't have to live in Manhattan, and you don't have to have a huge house, and 250K will take you pretty far. Other than real estate related issues, NYC isn't actually all that expensive.
