I totally understand the different answers and will try to analyze the best way possible.

@Tim Phillips I'd agree with your friends - rentals within driving distance are significantly easier to manage as well as decrease risk during the purchase process (because you can go see the property in person easily).I'd advise you to analyze as many properties as possible in your chosen market so that you have a good feeling for what a good deal in whatever market you pick is.

Every month, we like to analyze all of our markets across Central Florida.

Any other suggestions for analyzing the quality of the offering and the group making the offering?

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

. #3 Start working with an investor focused lender / realtor / property manager and get good at analyzing numbers. #4 Once you're comfortable with everything and you find a deal you like, pull the trigger.

I wanted to share some exciting news here at BiggerPockets as we have launched a new downloadable spreadsheet for analyzing short-term rental deals.Once you pull in some numbers from a STR data source like AirDNA, Rabbu, Mashvisor, etc., you should be able to see if a deal pencils out for you.

Events can be lucrative but may require additional investment upfront.By focusing on these metrics and carefully analyzing cash flow potential, you’ll be able to make a more informed offer and have a strong foundation for negotiation.If you need help with financing options or further advice, feel free to reach out!

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

It's a wish rather than an informed goal.I find it better to focus on systems/actions (analyze X properties, offer on Y, close on Z).