So it's like an on demand personal trainer.

Recover from torn MCL by sticking to PT then hiring a personal trainer to maximize accountability in the gym.

It’s easier to be a sales trainer than to be good at actual sales.

There are missing pieces from your scenario to see the true picture, but what I think you're implying is person A owning 10mil in real estate, heavily leveraged at up 80% loan to value, having an 8 million dollar mortgage and 2 mil in equity/networth. 

@Mindy Jensen I don't think anybody even implied your homes are bad investments, because your strategy is profitable and isn't applicable to the main point I made. 

He has mentioned a time or two that he doesn't sleep a lot and seemed to imply, to me at least, that sleep is a waste of time.

As many people have implied, only law-abiding citizens will heed your ban on firearms, and the armed undesirables will ignore it and keep their guns.  

So while you may be aware of the granular details of an area today, and that is important, it doesnt necessarily imply those conditions will remain constant throughout the holding period.

Maybe you could do your own business as a trainer for rock climbing(maybe in a gym or close place). 

Being frugal does not imply she is stingy.