If you followed his advice and not bought a house you would have had 2 less emergencies. Also, renting in the city you would have had no need for a car and thus 0 emergencies.
Yep I was going to add this. It sounds like he doesn't care if he has 10 huge houses or not and renting works just fine for him. Although he should thinking about hedging with some real estate, but I guess he probably already does that :)
Now he can almost afford to rent a 3 bedroom house in Los Altos Hills or Atherton... (Just kidding, there are no 3 bedroom houses for rent in either place.)
Then you have to worry about maintenance and upkeep, utilities, taxes, cleaning, etc. He also wouldn’t get the free breakfast and the optionality of moving from place to place.
I would question his financial acumen if he doesn't have a mortgage. Houses (specially the expensive ones) are a bad place to have money parked. Although, it doesn't make any difference in his fortune, anyway.
He works a lot, he wants to go out and party and go to fancy restaurants with the rest of his time, and he has most of the things he would use a house for in his office.
If you compare his life to how he would use an SF-size apartment given his lifestyle (not how you, or someone else would live) it is quite possible he's not really losing all that much. He also has no commute between work and sleep, which is a huge quality of life bonus.
You need somewhere to live. He needs to get somewhere.
Neither house nor private jet is an environmentally conscious choice. Either way you've both told every other inhabitant on the planet to suck it, you're getting yours.
I believe he does account for rent/mortgage, by doing an RV. And his idea is that he has handled retirement--he's living in retirement now.
The catch is that he had six figures saved up beforehand (he lives off the investment income), which doubles as a rainy day fund in case of serious illness.
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