Get to know the local rules, zoning laws, and Airbnb guidelines to stay on the right side of regulations.

Any knowledge sharing is greatly appreciated.  

Also not planning to hire a management company in the beginning.From your insights, my tenant to have a renter insurance, and I need a general liability and umbrella policy to add up.Thank you for sharing your knowledge!

Is it merely a speed and knowledge issue? 

You need knowledge of foreclosure law in your state as well as rights of HOAs.

However, she wants to stay in the property for a year. 

A knowledgeable VA lender can provide guidance tailored to your unique circumstances.

I’d like to hear from someone that has first hand knowledge that has done this recently in Florida.  

fresh real-time data is ESSENTIAL if you want you and your investors to stay ahead of the curve and know trends before they are widely spread, which in turn will make your investors happy which will make you look like a safe bet in their eyes, so real time data is IT 

Someone gets injured in the basement your home owners insurance probably will not cover it and the liability would be pushed back on you.Would suggest discuss the finish with a Licensed Contractor, Licensed Expeditor and maybe a zoning attorney in regards to adding a unit to current zoned two unit converting to a 3 unit.Also, when buying a two unit and converting it to a 3 Unit, read your documents with out knowledge of the conversion the bank holding your mortgage could call your mortgage.Let me know if you have any questions.RegardsJoe Scorese