There is a property I am interested in, and it will be auctioned at the courthouse next tuesday, so I order a title search.It shows only 1 lien for $amount (I don’t know the current balance of the debt), originally taken out by Barack Obama and later the loan was assumed by Donald Trump when he bought the house from Obama.

I'm pretty sure Cash on Cash implies using debt.

I also owe about 20k in non-mortgage related debt. 

, or should I take an equity loan and go further into debt?

That debt will be settled out of my own pocket after closing.The moral of the story is to find a competent attorney that understands what you are trying to be do, so that all of the proper documentation can be created and filed. 

Descendent had a reverse mortgage and just a few more thousand above that in creditors debt, ( she filed herself to avoid admin fees and such).

I also owe about 20k in non-mortgage related debt. 

In most cases, they just don't trust the investor.What are investors trying to accomplish with "buy like rent, lease option, option", In most cases it is to BUY TIME to find an assignee or to flip the property.Here are some ideas you may want to try on for size:Write a contract of sale (I use a skinny contract, one that anyone can read and understand in a few minutes) with a delayed settlement (for as long as you can negotiate), with right of possession or if occupied right of entry), and "subject to the existing mortgage"Skinny contract of sale with a Study Period, with right of possession or if occupied right of entry.Make full disclosures 1.

Just remember, you will need to buy a new property equal or greater than your sale; encumber new debt for the same or greater value than your current debt; and put all the cash from sale back into the deal. 

But if you are renting 3 of those units for $855 each, then you are using other peoples' money to pay your debt and live for free.