I think we need to see his balance sheet to understand his financial situation.
If his financial assets exceed the amount of mortgage debt secured by those properties, he may well be in good shape, financially.
You would also have to look at the cash flow. And the rental income he gets from those properties. Again, if he’s getting cash flow and rental income, which is enabling him to pay the mortgage, and all the operating expenses , he may well be doing well financially.
what you said ... bears repeating ...