She is obviously much younger than him so
of course they had to have a baybee.
It sounds like they are having fun and somehow surviving with a baybee. But they are completely dependent on others (not good) and as far as a career goes, you can't leave in 2008 and expect it to be easy to return for any reason. They better hope there are no injuries and that they don't have to go back to work. Also, what happens with school for the kid? And all these years this guy hasn't worked---what about social security? I'm guessing they don't have health insurance because it would cost a fortune? It would be difficult to do permanently this without a brat in tow, the stars would have to align perfectly. But with a brat? They'd better have a hidden source of income/money pot.
Maybe the guy invested his money from the Microsoft years and is letting the interest compound while surviving on the donations of others. Something about this seems disingenuous. More often though, people who make high salaries spend every penny they earn because most can't /won't budget. I've known of numerous people who earned well into the six figures, were laid off, pissed through any company-given separation benefits without lowering their expenses and had to cash out their 401K to pay basic expenses. Most couldn't survive six months, let alone a year. I think part of it is when a recent graduate happens upon a really good, high paying job and figures life can only get better. And this isn't always the case. Sometimes the high paying job comes with a on-call expectation and is highly demanding and after a few years a lower salary and work-life balance become more appealing.
I have a friend who did something similar, spent her 20's out having fun, traveling and working cool jobs. But there was no baybee to tether her either.