I am assuming with this scenario, the IRS would distinguish the property as an investment property, and not as a dealer or developer property if the intent is to reap the rewards on the property appreciation. 

Also, being that Florida is a common vaca destination, you also have the opportunity (depending on your state/local ordinance) to turn them into short term rentals (like AirBnB) to obtain an even higher returns!

Expense/Net SheetMonthly Income $7,070.00Monthly Expense Utility $190.00Lawn Care/Snow Removal $25.00Trash Removal $67.00Advertising $0.00 Craigslist and signage in yardInsurance $235.00Odd/End Repairs $75.00Total $592.00Yearly Annual Income $84,840.00Yearly Annual Expense $7,104.00Property 2014 Taxes $14,844.46Yearly Profit $62,891.54Unit Bedroom Bath Stove Fridge Dishwasher Microwave Washer Dryer409 #1 2 1 Y Y N N N N Y 2008 2001 2002409 #2 2 1 Y Y N N N N Y 2008 2001 2002409 #3 2 1 Y Y N N N N Y 2008 2001 2002409 #4 2 1 Y Y N N N N Y 2008 2001 2002401 3 2 Y Y Y N Y Y N 1997 1997 1997403 3 2 Y Y Y Y Y Y N 1997 1997 1997405 3 2 Y Y Y Y Y Y N 1997 1997 1997407 3 2 Y Y Y N Y Y N 1997 1997 1997Garage and Common Area Electric is paid for by Landlord *I assume this is the $190 / month utility figure listed in the monthly expenses.*$208/quarter for dumpster *I'm not sure if trash collection is this or if we have to add another $70 per month for the dumpster.

It can work in certain scenarios but this is not one of them. 

This is a very very common rookie mistake.I wrote a blog about that here in BP here.

I posted the article not because I agree with it, but more so because it's not particularly common to find an article exclusively about Denver in the NYT.  

Any possible pitfalls that aren't common sense or not figured out until in the thick of it.

What is the worst case scenario I'm looking at if property goes to 100% vacant?

I will give you the caveat that I have enough cash and Heloc money leveraged against my other properties to buy more than one place at a time so I'm not dependent on selling a reno in order to buy another but being more particular about the deals you do and making money by leveraging all of the advantages including lower taxes has always been a successful strategy.Both scenarios can be winners but you have to decide where on the experience/risk scale you are and I'm a believer in pounding out all the take home money you can get.  

Example Temple scenarios: 1990 yr built, 90k price home, 1100sqft, 3/2/1, $1000-1200 rent. 1955 yr built, 50k, 800 sqft, 2/1, $650 rent.