Talk to people there actually doing deals.

Potentially buying the property 5% or more above actual value.

I think if you meet Safe Harbor and you actually make "meaningful" qtr'ly paymets, you'll be good. 

Or is it better to charge rent before their actual move-in date.  

All you need is a few busy bodies who want to make trouble and you are effectively banned.In the Florida Keys, all but 2 of the islands allow STR for 28 days or more - how many folks can actually rent for a full month?

You might be stuck with this bill for a long time even if you get a judgement.You may actually have some trouble enforcing this given a year plus of this practice.

@Dave Foster awesome, I was actually unaware of the primary residence exemption so that could work out even better than 1031 I think.

Hah my real estate buddy is actually going to Amsterdam next week. 

It's actually funny....I heard the news break about the 'good economy' while listening to a show on Sirius POTUS channel with a national expert throwing out depressing numbers about the huge numbers of people living paycheck-to-paycheck (40-something %), and the increasing popularity of using these Payday Loan places (12-something %)So no the economy is not doing that well, but they can cook the books to make it look good (and both sides do)....

It is going to be more difficult than you think and it is going to yield a lower actual (spreadsheets are not real life) return than you are expecting.