At 50 yrs,  how should he approach for a 30 yrs mortgage having the kind of history with properties he had. 

I give them to my mortgage broker who pulls their credit every 6 months and asks them to fill out a mortgage application and provide all the necessary proofs.

Is it as simple as finding a property that is listed for a price that is cheaper than what it’s actually worth?

I have it rented for $1480 with a mortgage payment of $812.

View reportJust learning how to use the calculator.The calculator is using the initial purchase price as the driver for the mortgage.My intention would be to buy it and rehab it, so I'd want the mortgage to be driven off of the ARV number.Anyway of doing that on this calculator?

What is the process like if we were to want to subdivide while having a mortgage? 

Our goal is to get our first home and stay mortgage payment free while learning to manage properties for the first time, then to take that experience and invest in the more lucrative out of state areas.

I applied for a mortgage last year and my rate was 3.85.

@Matthew Hall I definitely have some insight on some cheaper ways to start out with.

It would be even more advantageous for you to rent out a room in that property to ease the cost of your mortgage.