In my case, as a DIY landlord, I'm in this for Cashflow Forever and Real Freedom.

As far as living a life of financial freedom with one rental- that is unlikely to happen.

OP obviously randomly bought a place, using hopeium as primary power of analysis, and to no surprise things did not end well. 

Lending would cease over night and government bailouts would commence.In my area of NE Ohio we are considered disaster free and generally we do not have any of the catastrophic issues that other parts of the country do... welp until last week when three tornados rampaged across three counties ripping down trees, power lines, roofs, siding, and putting over 500k people without power for a week - some still don't have power nor will they until all the trees are removed from the power lines. 

More power to you.   

My background is in Military and IT, but I’ve recently shifted my focus toward achieving time and financial freedom through real estate.

Which currently does not have a renter due to Power company messing up the yard and sewage system.  

I believe in the power of mom and pop multi family How did you find this deal and how did you negotiate it?

The year's lowest priced small multifamily sale on Long Island is $430,000.If you want to househack a multifamily, you'll want to find ways to boost your buying power.

It's amazing to see the next generation take an interest in building wealth and understanding the power of smart investments from such a young age.