I have some financial info on the tax return from 2015 from the landscaping but it is minimal.  

Minimal chance at appreciation on the property/market.I might be more willing to buy in a hotter market as an appreciation play on a property that is breakeven cash flow if I can use some of that depreciation to help pay down taxes on my other property.

I actually think we are leaning towards moving a small historic house onto the back of the property - found a big time developer that is going to cover the moving costs, because he cant demo the house, so the net cost to us is pretty minimal. 

We plan on considering the side work (GC and design stuff) to be taxable wage income but that is minimal compared to the profit we receive from flipping.

Vieques got incredibly lucky and there is no major structural damage and minimal impact/disruption to the island - considering the size and force of Irma. 

Of course I could email the realtor back for clarity but I wanted to ask here first because I also interrupted this email as a "start showing us money or stop wasting our time."

If the house is not habitable (regardless of the cause), then my understanding is that the tenants do not pay rent during the time the house is not habitable.Hopefully your insurance has a Business Interruption or Rental Interruption clause that you can invoke so that the insurance company essentially pays your rent during the vacancy period.Once the house is habitable, tenants should continue their rent payments.

You'll minimize your risk of failure and improve your probability of profit/success with a larger reserve. 

Have some patience, you will most likely be talking to engineers with minimal English skills, so keep that in mind.

It's $1, can't imagine there's much in property taxes for a vacant lot, so I could "enhance" the value of the property that I have for minimal cost.