You'll end up spending countless hours trying to analyze all the numbers, and in the end you still won't know what house to buy.Our grandparents didn't have all these research tools, podcasts, books, and other resources, and they still managed to invest in real estate. 

After analyzing GIS data, I discovered that my neighbor’s house, garage, and shop are built with minimal permissible setbacks (50 feet to an inch) from the boundary line.

I'm currently analyzing a potential rental property in Houston and trying to quickly estimate insurance costs.

BP has various tools to help you analyze your deals (rentals, flips, wholesale, etc). : https://www.biggerpockets.com/investment-calculators7.

It will just be important to identify the new property and make sure you stay compliant with 1031 exchange guidelines.If you have any questions on the tax piece or need any help analyzing the numbers, feel free to reach out.

Is there a rough percentage that you use when analyzing? 

@Grant NashI have no experience in flipping/rehabbing and will attempt to analyze strictly on numbers.  

I think the major branches of STR that owners need to know are -Financing, Market Research (you technically have it already in Cape Coral), Property Selection (what makes good STRs, regulations, analyzing, etc.), Designing and Furnishing (amenities, design, theme, linens, etc), and operating (Insurance, Property management or self-management, Tech & Tools, Cleaners & handy people, etc)All of these could be covered depending on who you work with that can cover each topic. 

BP has various tools to help you analyze your deals (rentals, flips, wholesale, etc). : https://www.biggerpockets.com/investment-calculators7.

BiggerPockets also has a calculator to analyze deals, and I highly recommend you start this as soon as possible, even if you are not ready to buy.