I’m thinking with the money out of that house I can buy around 4 homes around 40 k each to generate me around 800 / mo per unit meaning 3,200 a month in total gross income . ( I know this is true because I just bought a home for 40k and am renting it out for that much ) If you were in my shoes would you refi the condo and get 75% out to buy more homes or would you sell it completely for 100% and use the 160k to buy 4 units?

If I were in your shoes, I would research markets where you want to retire to.

In your post you say that Trump assumed the loan when he bought the property but mention in your next sentence that the bank didn't know about it.This means that Trump bought the house "subject to" the existing deed of trust without the bank's permission.When a person "assumes" a loan, they are getting permission from the lender to step into the borrower's shoes to take over the loan. 

Gas the car up and put on your comfortable walking shoes pal! 

Today I'll suggest you put wool socks over your boots or shoes so you don't slip on the ice!

So if I were in your shoes, I would definitely have no problem taking applicant 2 and telling applicant 1 that its already taken.Better for you that you make that call than for you to wait and then them tell you they can't make it and applicant 2 tell you they've gone with another house.

Taking into consideration and putting myself in an investor's shoes makes me understand how they think and can render pretty valuable inputs.

Have any of you guys been in our shoes before? 

If I were in your shoes, I'd pass.

When I think of owner financing, I put myself in the sellers shoes and think that they wouldn't want that and would want their money upfront, so I already rule that option out in my head.