The problem with this is that it moves in the wrong direction. You spent all this time learning how to earn more money for your time. Then what do you do after you earn a bunch of money? Figure out how to trade your time for money again, just in different arenas? Why, so you can avoid having to spend more time doing what you specialized in? This isn't the direction of leisure.
The MMM types always are quick to say that they actually enjoy all these little things they do to avoid having to put out more money for daily essentials. Cloth diapering and seems the be the poster-child for these sorts of things. Also using single-blade razors. Working on your own car.
Doing these things properly requires learning more skills. But time spent learning these skills is time not spent engineering. It almost seems more of a irrational reaction against modernity than it does an actual path towards greater impact.
You need to be trading the money you're making through specialization for time not spent learning more skills to be going in the direction of more actual leisure. (what I call "fuck you time". Much better IMO than fuck you money.) You use some of the freed-up time to make more money, and the rest of it towards leisure activities. It's possible for your skill-set to be so valuable that you can maintain ridiculous incomes on, as Tim Ferriss puts it, four hours a week.
Every dollar I can spend on not learning a new skill is a minute I can put towards pushing my flywheel.