Sounds like your friend did something wrong with his investments. I had rentals before 2008, and bought more during the crash in South Florida for pennies on the dollar. It was a great time to buy.
Having family in Cuba, I guess this could work, but it doesn’t scale, because someone will inevitably steal your horses for dinner, when you aren’t looking.
Bus driver in SF or near a tech hub, so I can listen to mindless grifting and endless complaining by tech workers that would re-enforce the life decision I made.
Those people still need to rent. So as long as the rental income covers the mortgage, you’re ahead of the game and someone is paying an asset down for you.