I highly recommend investing close to home because of the great Chicago Real Estate Investing.I love the book Mindset, The One Thing, The Power of Now -> all more mindset books but I believe in mindset first and then investing!

@Aubrey E Alleyne I am not sure you can go wrong being that close to the beach.

If purchasing the land will not require the permit to close but will require plans If refinancing on land that is already owned will require the permit 

The very few builds that have sold that even come remotely close have sold for a fairly nice premium. 

As far as location, it is very sought after as it is is very close to the airport, easy access to the Space Coast on the 528, the 417 will take you right to Disney and downtown is just West on the 408.

If this is a refinance, a lot of lenders are looking at values more closely and will either agree with the appraised value, require a secondary report, or just cut the value all together. 

Management company is crucial they must be willing, close enough to see it and honest.

The good HML companies will look at the project closely with you, to make sure they think you're on the right track. 

I have heard that paying off your rental is not necessarily the best choice because of the deductions it allows for, but given the type of loan this house is mortgaged with, is it even possible to buy another home together and start renting this one out when I have a FHA loan on this one?

You might still be able to double close deals.