Or plan C. For younger engineers start thinking about financial independence. Software Engineers enjoy a high starting salary and an even higher mid career salary so it is entirely possible to achieve financial independence in your 30s-40s with a frugal lifestyle and smart investing.
Ya it is hard to say. From his POV - he is already "retired", so he has tons of time available and if doing things himself limits his expenses - win win.
For someone who is busy working.. it depends. If you get a salary to work 40h a week... does hiring a poolboy for $20 an hour instead of cleaning your own pool for a self-declared time worth of $50 an hour make sense? I am not sure. If you are consulting and your choices are bill 45h and have a poolboy, or bill 40h and have your own poolboy... then the logic is much more in favor of outsourcing your tasks.
The other trick is how much do some things really cost? I know to pay someone to put brakes on my car, I would pay the equivalent of $100-$200 an hour. For $100-$200 an hour, I will gladly crawl under my car and get dirty!