One more piece of advise to help make up your mind in the "pro" column: Georgia and Florida have started looking into the legal gray area of wholesaling without a real estate license.

My first piece of advice would be to always be networking with other wholesalers/investors both online and offline.

The only piece of advice that I would give is that getting a STR to market is death by 1000 cuts.

I am glad you highlighted the management piece as this is a crucial part of buying in another market.Excited that you are stabilized and are generating cash flow on that deal. 

Much of the negotiations during due dilligence depend on demand for that specific property- hopefully your agent has build leverage in to your contract that they can use to help you with this piece. 

You’ll sign a piece of paper at closing saying you plan to live there ], usually within 30-60 days.

My best piece of advice is find the most nit picky building inspector you can.

I found this deal while looking at the deal next door which was a larger piece of land.

Quote from @Brian Christinakis: Let's not forget the liability piece that STR insurance provides in MUCH higher liability limits for incidents ON your property but also incidents off your property while your guests are staying there (like using a bike).

My number one piece of advice is finding a group that you can attend online or in person to keep you motivated and accountable to your goals.