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!
He advocates doing things yourself, DIY etc.
If you can pay someone less to do something than you could earn in the same amount of time. Its better to outsource those tasks.