@Dylan Speer sell it, come up with the negative money balance, write the loss of on your taxes and move on with your life.You can sell it "subject to" to someone looking for a home with no money down and save on Agent commissions?

@Nicholas Pisano real estate investing is a long-term game, not overnight.Have seen many newbies jump in a buy several properties, then when things don't go according to their unrealistic plans, freak out and sell at a loss.A past client is doing that right now - they bought 5 properties from a high-pressure agent, hired us, micro-managed us to try to meet their unrealistic expectations, terminated us and hire another PMC to "save" their portfolio and went that didn't work out, are now selling 3 at a loss. 

Plus if you want to do the STR loophole and offset your active income with "losses" from your STR, you will need the losses to flow to your personal tax return.

My worry is always having the means to be able to take care of that monthly loss down the line.

You are already losing money on it so you should either cut your losses and sell or be comfortable losing money on a monthly basis with the expectation to make it up on the sale down the road (see you're in FL so you might need to wait a few years).

If you can break even or maybe even take a small loss going the permit route, that is probably the most prudent option.

I assume you mean Return on Investment, like this:ROI = Net Profit or Loss/Amount InvestedI don't believe this is an appropriate way to evaluate a flip.

They follow state laws, or in the case of a VA loan, the borrowers entitlement will be reduced by the amount of the loss against the loan.

You are correct, All of the standard Market companies I contacted would not write the coverage with an open loss.  

Traditionally, the courts give a lot more weight to what actually happened over what is written on paper.