Most friends I had when I was younger that made lots of money and had big houses and boats or multiple houses in other areas were business owners of some sort: contractors, owned electrician businesses, large landscaping companies etc. Also people that have big families where one is a lawyer one is a real estate agent one is a property manager and they set up big real estate ownership groups. Of course all the doctors and such. You also used to be able to live a pretty lavish life with a low 6 figure income you would get by being in management at any company on RI or nearby MA, or a chief of police or fire station... not really possible anymore. At that point you're still upper middle class at best.