None of these communities will be changing to residential neighborhoods, although a couple do have residential 'sides' that full time residents live in and can not be rented short term.Two of the big communities that you will have some issues with self managing are Reunion and Margaritaville.

Rev Proc 2008-16 does create a safe harbor for your investment intent at 2 years of investment use coupled with  some other qualifiers.  

Quote from @Luke Tetreault: My Fiancé and I will be wrapping up our 2nd year of investing part time in the next couple of months.

A couple of issues you need to be aware of are any ordinances that are in your town or coming up.

Right after I closed on that one the insurance company demanded I make a couple thousand dollars of repairs.

I'm out West at the moment, but will probably be returning to Tokyo before too much longer.At the risk of being contrarian, after picking up a couple of investment properties in Japan (one Tokyo, one outskirts), I shifted to a strategy of only investing in the US. 

@Loren Souers Couple of questions. 

A couple issues with Credit/income on paper.

I have tried a couple and didn't think they were very helpful.   

I have been listening to BiggerPockets for a couple of months now and have been doing my own research over the past several months as well.