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.

Check their communication style - do they respond promptly, comfortable with video calls, and send regular updates?

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. 

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

If you put yourself in the lenders shoes and think about the risk of the deal and worst case if the borrower defaults what is in it for the lender?

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

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

I'm having trouble finding a tenant that I feel comfortable leasing the space to.

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.

Too many in your shoes over complicate real estate and spend unnecessary time and expense on tax planning & asset protection and in doing so, take away from the real estate.