Of course we all want the best of both worlds; that is a hidden gem on a secluded/private beach, but close enough to a town to find good eats, drinks, and shopping.

thank you.Hi Jessica, I will say that if you're investing in California, you won't be finding any positive cash flow and it will be purely an appreciation play for the most part. 

But if your family instead was going to use it often, then you pivot from looking at it as a pure investment to looking at the value of your family’s togetherness and happiness.

They already are given their utility allowance on a debit card instead of via direct payments to the utility companies, and lo and behold, none of them magically ever have enough money to pay their utilities, but they have plenty to host parties drink smoke get llegal pets that trash the place far beyond what the security deposit covers...so I can't imagine how much money is getting pissed away in Florida.

I would echo what many other people are saying - decide what your reasons are for purchasing, is it purely based on returns or is it somewhere you'd like to also vacation?

The more common one I'm seeing is just pure speculation that the value will continue skyward in the future.

Was having a fun, purely academic conversation with someone and somehow the topic went from the stock market, ETF's, to real estate, to BRRR's and either he or I or both us came up with this and wondered is this a legit strategy that others have used?

That looks like your problem - only 3% down (can you get that conventionally if its a pure rental property - i'm not 100% but I don't think so) - with that leverage (97% LTV), pretty much nothing is going to pencil.

In other words, how would I calculate the return (from a purely financial standpoint) of "investing" in a primary residence vs renting and putting the money elsewhere (perhaps even into an investment property, but also considering buying a business)? 

Seminole for Example has a lot of great traffic and tons of spots to eat, drink, socialize for adults and kids.I know Cape Coral is picking up in terms of STR's with the complettion of the 7 Mile Island and more construction lately.