There are a lot of hotels right now that are failing and going under due to low cash flow -so its a failing hotel.

The rent plus his retirement will actually produce positive cash flow.

Ladder them up so they sell at different times so you'll always have cash flow coming in. 

They all cash flow and are easy to manage (so far).

If you buy in a good market, appreciation will beat cash flow every time. 

The real property investment can be repositioned if it proves disappointing in its original form; it can be refinanced or recapitalized if it has too much or too e pensive debt; inflation over time bales out many bad purchases, and finally the investors knowledge, experience and abilities can be leveraged to turn around a cash flow negative property.I’ll provide an exampleThree years ago we purchased a note from a bank secured by two auto repair facilities with a large amount of excess land.  

@Jeffrey Mair I would keep your rentals forever, especially that they are cash flowing. 

 @Jessica Frisk I would not be keen on the 15-yr fixed rate mortgage if that makes you cash flow negative.

It just might be a different strategy involved.Cash flows through refinance or sale or operating cash flow is the same in my book.  

There are many reasons that adding a single ADU in southern CA is a less than ideal RE investment (i will post a list at the end) but the negative initial equity is a primary reason as the initial negative equity position consumes the initial cash flow and can take many years to recover.As for converting your home to a rental….