Quote from @Stephen Magee: Out of state investor here - just purchased a duplex near Naples botanical gardens.

This will help guide your decision opposed to investing somewhere for a novel reason.for example for me it was cash flow, price to rent ratio, land lord tenant laws and availability of multi-families(Just to name a few). 

But it's a lot of work.  

@Fab Ragh @Andrew Street I can definately provide a lot of insight into all the major resort communities around Disney.

Unlikely to find a GC though.

Quote from @Nithin Thampi: Is there any site, company person I can pay to analyze a game property from a property management company?

The upside of the higher priced markets is a higher barrier of entry which keeps a lot of people out.

I would sell that property in IL and chalk it up to a learning experience.

Melisa Justice, and she helped me navigate the entire Journey, it was a process not too long, it took about a month, and the process would have been definitely very hard being that I was on a different state by Melissa made it a lot smother, she was very responsive to all my questions (and I had a lot of questions), she helped me find a lender that would fit better for my financial situation, once I was pre-approved she connected me with the right property inspectors, and all through out the process she kept in touch pointing me the right direction all the way until closing day, all this to say I Definitely recommend her for any body the is finally ready to take the plunge and get started with their real estate carrier, I definitely will get in touch with her when I'm ready to buy my next property!

@Chris Seveney This reminded me of a line in a John Mayer song: "When I really start to break it down,I wouldn′t trust a girl who knew about this place."