A vast majority of the work will be done by myself and a few close friends.

I've just started to scratch the surface of the vast amount of resources available here, and I am very excited to meet all of my future friends here in the BP community!

I'm new to this as well, so I'm going to leave the ROI analysis to others but, one thing I will say is that I think you're vastly under estimating the amount of taxes you will owe.

In my view, homeowner's insurance + umbrella + professional property manager should be good enough to (i) prevent lawsuits and (ii) protect you sufficiently if the worst happens. 

@Hunter BylerA minimum of 6 months seasoning before lending off an appraised value is a form of risk management that the vast majority of lenders have written into their guidelines.  

Given that I will be considered self-employed and will initially not have income (or at least not income that is steady or predictable), I will be having my parents co-sign the FHA loan to fulfill the income requirements.I clearly have sufficient capital to not only fund a 3.5% down investment, but to also make the subsequent mortgage payments.

You stated that very fact yourself and you are now simply living the reality and yet still surprised.As for contractors...the vast percentage are unreliable.

We have sufficient funds in our account at all times to cover our cash flow needs.

Sure - as long as the benefit of the Series is sufficient to cover those costs. 

Zillow and Redfin should be sufficient for pulling sold data as this is public record and you do not need MLS access to view it.