If they say you can afford $3500/mo but  you know that you like to have money for eating out a lot, concerts, travel, whatever, then be smart.  

People come from all over to tour the bourbon facilities, the concerts, river events. 

Triple A baseball, minor league hockey, concerts, plays, etc.

However, it's still the closest thing to "Vegas" on the east and seems to be pivoting towards an event/vacation driven economy. iE hosting concerts, conventions, sports tournaments, amateur fights, ect.What are we missing here?

Unfortunately her being my sister I also know that in august/beginning of september she went on 2 vacations out of state, the state fair, a concert and the county fair...so she is NOT struggling financially she is just putting rent as her LAST priority!

I would trade 2 hours of euphoria coming from Journey/Def concert any day for a lifetime of lessons and advice from these two real estate giants.

Keys was also very seasonal while south Florida is a hub for events, conferences, concerts besides the typical beach/partying which means there's always an influx of travelers whether for corporate/family or spontaneous getaway.If you find something in the Keys you will make money regardless - I just found this area more profitable.

I have made a concerted effort to diversify my exposure into cities with more promise, but so far it has been a lot of work with little treasure.

I believe there is a concerted effort by many to attack this problem I would join that group.. 

Or maybe event space, urban fitness course, concert venues, testing facilities, food courts, skate parks, breweries, education facilities or start-up incubators.