One thing I've seen is that when people do a strategy like this to get themselves out of debt or reduce it, they haven't changed their financial behavior and wind up back deeply in debt but having already utilized the asset are worse off than before.

He is very risk averse and extremely happy with the results.The main question to ask is do you want debt or equity partners?

(maxes out cards and a couple missed recent payments)  So it’s either stay with my current mortgage and try to slowly pay off my debt Or sell and start over..

They lost track of it on their tax rolls, thats why they didn't sell the debt or foreclose on it.

I have no interest in going to college and putting myself into debt or owning a home that will not make me money, atleast to begin with.

If you are paying off credit card debt, or buying another investment property are good options. 

I will not be forgiving rent or debt, or giving any discounts.

I know obviously there are certain things that go into it such as credit score, amount of debt, or how much in cash reserves I have but if all of those were flawless could the max be 75%.

If you're not in debt or on a tight budget, there's not really much there you need. 

For example, do they have 15 store credit cards and tons of credit card debt?