I've been trying to pivot my investing and instead of saying "I can't afford it," I'm trying to change my mindset to, "how can I afford it."

Has anyone done or entertained this for a strategy to profit?

I guess if you are worried about building your team/people you trust to manage and look after the property may want to find some markets that are affordable and easy to travel to and from NY so you can go visit the property need be. 

Have read many people from Cali docking to Phoenix for jobs and more affordable housing.

This is all I can afford and want to get a portfolio/equity going.

Any insurance in FL, especially wind is likely not going to be cheap.Look for affordable coverage that will also bring you great value if you have to make a claim.best of luck

On the other hand, the economic factors like interest rates, affordability, and supply could make the sf home only increase in value in the short term. 

I can't afford to refinance it into an investment type loan because not only will it be more in interest rate but also my down payment has to be a lot higher and my monthly payment will be higher in which case I can't cashflow.

However If you can afford to do that, that works too! 

In the worst case scenario with a ban, the property wouldn't cash flow that well (a few hundred negative).I am comfortable with that considering this scenario still cash flows better than most other housing arrangements I could afford in this market.