I have researched this issue and am aware of the tax disadvantages, and there is no mortgage, ie: no "due on sale" clause, and my state only has 10k in homestead exception.  

JD Thanks for the reply, I'm aware of the inspection/repair contingency in terms of backing out of the deal if rehab costs are too much, but would that allow me to be guarded against claims I or one of the contractors damaged something while on site?

Depending on the carrier this can be exclusive to Category 1 and above Hurricanes or it can also include Topical Storms and/or Tropical DepressionsTropical Cyclone - A little broader in that it will generally include any storms that originate from the Gulf of Mexico regardless of the status (hurricane, tropical storm, etc.)Wind and Hail - The broadest in that it not only covers any storms originating from the Gulf of Mexico but any wind and/or hail damage regardless of where it originated fromThe reason why you need to pay attention to this particular deductible is because it will be percentage based deductible; keep in mind that this means that if your cost of insurance on the dwelling increases, so does the deductible.

This is roughly an hour away from the tanant that shot his landlord last week over a $30 rent increase. 

I own a condo now and do not like how the HOA fees are so high and continues to increase year over year.

The one I ill advisedly bought when I got married for the first time at the tender age of 20, which was remortgaged once and has not increased in value at all since (and the taxes have gone up).

We're willing to increase our bid if we receive a counter, but we just feel this person can just as easily throw-in another $100k+ in cash....Anyone have any good stories of how they stuck it to an all-cash buyer?

I have money saved for reserves and maintenance, but this is a very low maintenance place.I am well aware of the expenses incurred in a rental property investment.

Current tenants lease ends November 2018.3) Maintain ownership in the property and get creative regarding increasing rental revenue and financing future deals.

Start there obviously and then increase price according to what you NEED to make.