There's no right or wrong way to do this, just varying levels of risk and the only proper route is the one you understand. 

The other thing to consider is the age and if you add a second floor will the entire structure need to be brought up to code for hurricane and wind.I live in a neighborhood where the homes are older (not in florida) and the foundations are hollow core CMU and adding a second floor would not be feasible due to soil bearing.

Move to FL and come work for my company.

There's been a few Houston developers on Biggerpockets podcast episodes.One that comes to mind is Donovan Adesoro. 

Welcome to the community and be ready for a huge amount of information at your finger tips.

The city has issued licenses, they are just very limited, hard to get, and there are a lot of restrictions around how it can be used. 

We host an investor meet up every month in Alexandria, VA.  

Can anyone refer a real estate investor friendly real estate attorney in the New Haven CT area? 

I've been pondering the same question lately.For items like HVAC filters, do you remind tenants when it's the time to change it, or just expect that they will do it?

HOA just pulled up 4 of my signs this week after courting investor client to buy there.