@Tim HoltFrom my experience, house hacking can work well if you focus on minimizing living expenses and setting yourself up for future cash flow.

The property has to meet very minimal requirements to be allowed to be rezoned (section C). 

I am surprised these lending institutions don't regularly run algorithms showing which loans have been assumed Seems like an relatively easy thing to do to regulate and in a way minimize risk - maybe have more defaults but still maximize their loans by forcing compliance 

The concept discussed likely assumes that you’re building equity through appreciation or loan pay-down, while any cash flow is minimal or neutral.

Overall, my primary goal is to create the opportunity to get into another home at minimal cost while keeping my parents in the current home, so I'm leaning toward transferring/selling the current property to them.

See if the Seller will finance with a minimal downpayment.2.

The hope is the tenant does not move and the older house that had minimal repairs will not fall apart anytime soon.So an old house with minimal repairs to it, questionable areas to invest in, and tenants that tend to live hard in the spaces can be a recipe for disaster. 

For the past 3 years, I've paid my property manager in Costa Rica via paypal, a minimal cost for me and he gets his money next day.   

Likewise, I’d need to work out how prospects would tour properties safely, legally, and at minimal expense.

I am grateful we attended the rich dad seminar because it is what got the ball rolling for us for a minimal cost.