If you are going to be an owner-occupant, want a low down payment, and are planning to do a renovation, the FHA 203k and Fannie May Homestyle loans are your best optionsHow do you know the property is currently upside down on the mortgage? 

Everybody thinks they can paint because they can - you get a brush or a roller, a can of paint at Lowe's and away you go.

There are other loan products available that are still a low down payment. 

Low value markets might be Pennies on the dollar like you allude to. 

A property manager’s expertise in handling maintenance issues, dealing with tenant concerns, ensuring legal compliance, and keeping vacancy rates low can make a huge difference in the financial performance and sustainability of a property.

Starting with a trailer is a smart, low-cost option.

I don’t want the property to appraise low and not have enough money to get when I cash out.

When rent is too low it speeds up the leasing.   

Low prices enable more people to buy, limiting demand for rental properties so rents decline (in inflation-adjusted dollars).Population Growth: In areas with growing populations, demand outpaces supply, driving up property prices.

Even if I were to rent it out on Airbnb, the cash-on-cash return isn't very attractive.Specifically, I’m concerned about:High mortgage payments and the financial strain it could cause if the property doesn't generate sufficient cash flow.Cash-on-cash return is low, even with high-revenue short-term rentals.My Questions:Risk Mitigation:Any strategies I can use to mitigate the risks associated with owning a high-value property with a large mortgage?