I'm currently house-hacking my first property but there's so much more to learn and I feel I've barely scratched the surface.

I also know people with "net worths" into the millions but barely enough cash flow coming in to cover their debt ratio. 

This guy barely makes enough income monthly to cover rent. how is he going to pay for other expenses like food car utilities schooling etc. after he uses up the proceeds from the sale. 

At that rate, $2200 a month would BARELY cover those numbers if/when you leave (that also isn't including PMI), and does not leave any money left over for repairs, turnover, property management etc.           2.

The property appraisers office has the the property value listed at just under $20,000 but because the home was built in 1930's and might need some inside work, it might be less than that but the big advantages is that it's on a paved road right inside town and near commercial properties, heck even if I could make $5000 profit from the sale after I took possession, I would be tickled pink.

I am sure somewhere here my math is a little off but bare with me.

As a company, the median percentage of annual rent spent by owners on maintenance does not cross the 4% threshold until year 8 in our Memphis management office and year 6 in our Dallas management office and then just barely.  

Barely 1 year old.

It is about them being conservative and safely supporting the bare minimum.

Financing larger properties in the  $1-$10MM range requires 20-25% downpayment so you barely have enough at the low end of that range.