I know...why would you dump it all at the same time?
He has 27 properties? Sell three a year. Use the proceeds to pay off the other mortgages or reinvest them into something else.
Have these people never used a pencil and paper to do “what if” excercises?
Might be a single apartment building with multiple units but still could sell fractional ownership fairly easily. But to answer your last question, I’ve found most folks are not that creative, especially with finance.