It sounds like you're comfortable enough to be debt free, but still chasing after something more, despite already having it right there in your backyard.
I don't think you realize how little money you need in order to have a fulfilling life. You can live in the nice neighbourhood and take a low paying, stable job, be frugal, get good insurance, and enjoy the advantages of your class position.
Pardon me if this comes off as overly prescriptive or nihilistic.