Probably find property that have closed, then cross that with the public record for which ones have a mortgage and the ones that don't cross are your cash deals.

If I sold at $275,000 I would be able to clear approximately $90,000 (that is counting the money I have already sunk in to the property).

There are some rules and regulations to consider with a 1031, but they're not as complicated as they seem and you'll need a Qualified Intermediary to assist you anyway, so they would help make sure you cross all your Ts. 

I was born and reared in Boston's cathedral of the holy cross neighborhood.

Or am I talking to traditional lenders who are just cross marketing into the hard money space?

Stop watching HGTV this dose not count as flipping education. 5.

I have heard other people say that lenders will count it against your debt to income ratio.

A lender once told me that car loans that have  only 10 payments remaining don't actually get counted in the debt to income ratio.  

Say to him that with the owner finance, he will still be making money from the interest, even though he wouldn't own it. the payments should not hurt his social security and medicare medicaid payments because he will not have to show the one lump some of income from selling it as it will be spread out through the years. and maybe suggest that he sets it up ( LLC or family trust) so that if he passes, that the kids or grand kids will get the payments and will not count towards their inheritance.

If you Cashout you'll probably be paying a higher interest rate than you are now (I'm assuming here, I have no idea what your current rate is), your insurance costs on the property may go up a tad and you'll have some closing costs, ensure you are counting for that!!