This implies the owner will sell the property for less than the mortgage balance. 

From your numbers above it looks like there is equity, so you would want to base pricing off the unpaid balance and not the value of the property.

@Ned Carey One of the required elements of a DIL transaction is that the mortgage balance exceeds the property’s current value.

Then when he pays rent on the 1st the money goes towards unpaid balance, fines first and balance on rent..

Flipping the home would result in a faster sale, which would pay off the principal balance due to the hard money lender upon sale- most flips are complete within 4-6 months if you take on an easier rehab and price the property appropriately.

Hope to get there someday...I don't think he was being negative, I think he was just trying to give me some balanced insight into that type of real estate asset class and some of the issues I should think about early on.

If your loan balance is at or below 75% LTV, you may be able to refinance to a lower interest rate.  

I'd recommend getting your personal balance sheet, tax returns, schedule of real estate owned, and resume available for these conversations.  

Investment is about achieving a balance between Risk/Return.

Any suggestions for choosing appliances that balance reliability and cost?