It's never because I am giving people bad advice or out to make them lose money.

There are some partnerships that are designed by nature to be short term, so there’s not as much to lose if things don’t turn out rosy.

Will Aunt Betsy lose her house and be forced to sell her body on the streets for the next fix?

And this is CRE, so it's cutthroat, it's no one's problem but your own if you lose an earnest money deposit. 

If I tried to base my renewal on expenses only I would increase above market rents and probably lose my current residents because of that. 

You mention they are a good tenant and if that’s the case, then I wouldn’t want to lose them over this.

if you just bought a property with it, for example, you would likely lose money on it forever.

If the market slows down even just a little...catches a tiny little cold...you will lose all your money and the lender will likely take a loss also.I ran a distressed debt fund for 5 years, DO Income Fund, and we had hard limits when buying distressed debt.

But then wouldn’t I be losing all the gained equity in our primary home?

Do I lose revenue - yes.