@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?

Also, there are no coverages for the most common homeowners' losses like water backup-- it's just standard coverages.3.Youshould get insurance as soon as possible -- there should be insurance on thecondo at all times.

You want the flexibility to access your money sooner.4) Tax Benefits from Real Estate: When you invest in real estate, you can take advantage of depreciation and losses to reduce your taxable income today.

@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. 

The tenants love her, she stays on top of maintenance, has implemented upgrades to improve the property and drive rent increases (much to my dismay, LOL), organizes fun themed events with catered food for tenants, manages evictions and oversees the building's Section 8 program.

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.

The package includes:- 3 nights at a 5-star, all-inclusive resort - All food and drink- Access to 3 keynotes and 60+ speakers and breakout sessions and guided networking - 3 evening events - Networking breakfast x2 and Networking lunch x2- Access to the exhibit hall, and more! 

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).

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

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