This is all sorts of wrong.My initial issue with Matthew's advice is that the property has only been owned for a month so unless the "wind damage" occurred during that time there is no covered loss here. 

From my experience in Florida real estate, I'd suggest confirming the repair budget is realistic—costs can often exceed initial estimates.

We have financing lined up, so now my initial question is, what have you all found to be your most successful way of finding good deals?

With the VA loan, although this is not an initial investment property I intend to make it one sooner or later.

I was excited because the price of the house and rehab was right, did not do any further inspections and completed the deal.Turns out my issue was deeper than the initial diagnosis.

There doesn't seem to be a lot of MTRs (rooms and entire units) in the area just based on initial searches on Airbnb and Redfin, but I understand this isn't the only indicator of demand.

Things continued at a snail pace with the rehab and I continued to remind and plead ABC to pay us the rent guarantees.ABC Baltimore promised to continue paying us rent even after the Rent Guarantee expired on Dec 17 2018 because the house was not ready after more than 16 months.

  $75k (initial negative equity)/$577 (monthly cash flow in this hypothetical case) = 130 months (10.8 years).  

Even without the cleaning fee the out the door price is still much higher than the initial ADR.  

They are telling me they can afford the rent per month but have a hard time coming up with the initial first last and security.