@Ryan Moyer - you also want to consider the opportunity cost of spending 6-10 months building a property that won't be generating any income.

House-hack = using your primary residence to generate income, making it a true asset. 

Which cities do you believe generate the greatest return?

As an entrepreneur it is your job to take on risk in order to generate returns.

I've read before on here about having a plumber come out to do a pressure test on the water/gas lines and electricians bringing out generators to test electrical.

I'm down to getting bids from 2 security firms, but still need a gate manufacturer and a security guard for random stops. 

Honestly Ask yourself if they called a random agent off Zillow would they net more or less than if you were involved.

They are often generated by agents doing CMAs, comparative market analysis, which is a method to compare properties to guestimate what the fair market value is.Fair market value is the value at which someone will buy the property within a reasonable time.

There are also other repairs at random times.2) The $150 only replaces the window. 

Best wishes to you.Soh I agree I don't want to drag this too much and sell to reinvest where it's actually generating income