We are also planning to start spending winters in warmer climates... 

Not only is it a recreational source but it is a climate moderator.  

And, with Trump we know that policy is lower taxes and a more favorable climate for business.

I'm new here so may not have a full view but the overall climate seems to be-anything to make a deal-ridiculous financing, leverage the home you life in-who cares where it is located it will be easy to rent/manage from hours away-don't be gracious with your tenants and housekeepersMy guess is a tilt toward young and not financially stable which is awesome if remaining sensible. 

Some markets may have more viability for success, but it's not likely to scale quickly or at all in the current climate.

Just wondering how you feel about the unique challenges NOLA has relative to economy & climate change (insurance), population decline.  

Is this unit in a warm climate where heat isn't important???

Chicago isn't going anywhere.Compare that to other cities in Florida, I think the population growth is amazing but long term with hurricanes/climate change, it will be harder and harder to own there. 

Teak is a tropical climate tree. 

I don't know how they can operate in this climate, especially with all of their challenges with this amount of overhead.