For the community development dept, you'll need proper plans (architect), site survey, permits, etc. when you're ready. 

The struggle comes when you plan to sell, pay close attention to how the bank would treat the loan in the event you would sell.Even though its a bit more work, banks are typically open to these loans as it provides them with additional collateral in the event of default.  

I am taking your advise, and switched my game plan to include a local agent or property manager to show the properties. 

I can imagine this is a challenging decision to make.My thoughts:When hope is a key component of the plan of action, it is time to cut losses.

It seems like it would be great to flip one property while planning on getting another one ready to add to my rental holdings.

They found it out, andI had to go to the planning board and zoning board, hire an engineer and architect to make the fourth unit legal.In my opinion, the realtor should have verified the zoning, and if you used bank financing, it's pretty rare for the bank to miss it as well.You are probably going to have to hire an architect to draw plans and to get it approved as a triplex.I wish you luck.

The demand for vacation rentals in places like Destin, 30A, and Panama City Beach remains strong.

Work with a tax professional (preferably a CPA that does tax planning and not someone at H&R Block or TurboTax) to ensure you qualify.

One of them told me they only have to provide 15 days notice, which doesn’t help if I am on vacation for a few weeks or haven’t checked my PO Box in a few weeks.

I have a similar project in Buffalo NY, however, I had to change plans when I got further into regulations.