We were boing to BRRRR in Ohio but decided to hold off on that as we didn't feel comfortable managing it from this far so held off on it.

If the insurance makes the numbers not work then yes walk, but if its more about the risk of being in a flood zone - 1/2 of florida is probably in a flood zone and its all about how comfortable someone is with the risk. 

But IF the property in question is in compliance with all code, and provides a safe and secure environment, all problems are timely addressed and corrected, and the property is maintained on a professional level, then the investor who has a large capital investment in the property should be entitled to enforce any contracts providing him with the agreed to cash flow. 

I didn't see where you factored in a $3000 mortgage payment (principal & interest only) in today's higher rate environment. 

I believe we are in for a very active real estate environment.

As for leasing, I feel comfortable in that area market to get $14/sf.

Trying to make myself more comfortable with hiring help for setup. 

Then, compare those returns with the stock market’s historical 8-10% long-term gains to evaluate whether the investment makes sense.Also, consider whether you can comfortably cover the $1,000 monthly shortfall.

Since I have damage protection waiver in place I feel more comfortable asking for a smaller deposit.

Get out of your comfort zone.