I understand it is a lifestyle many would envy, but why call it privileged? He may have sacrificed 10 years in grad school, incurring a large debt. How is that privileged? EDIT: Re "lavish" I would say that living off dividends or interest is a lavish lifestyle, a lifestyle of freedom, unlike living paycheck-to-paycheck, or off the principal.And my point was that with respect: you do live an incredibly privileged life which from many people's perspective could be considered lavish. You have a large pension fund, you own property and you have savings in the form of a college fund with five figures worth of money in it. Sure maybe you're not living a constant life of consumerist luxury because you're making smart choices, but I don't consider this in any way struggling and reiterate the point made earlier that it would be almost insulting to suggest it's so given how much of the population enjoy so much less.
What is sad is that what you're describing is the standard middle class cultural narrative (I am from the UK but I suspect the US and UK are in line on this one). Forty years ago home ownership, savings, pension funds etc were all pretty standard even if just one partner was working in a standard job. Now, especially in cities, this is a pipe dream for anyone who isn't earning significantly over the average.