Most of your serious contractors wont pay the extra for Lowes and HD delivery.

The contractor generally gives you a firm price for a finished job , contractor will charge extra for rotten wood replacement .

Are there any brokers, investors or agents in Florida looking for an extra free hand to help assist with anything?

If you, the homeowner pulls permits on the home, you will sign an affidavit that will prevent you from selling the house for an entire year.

If you can put hurdles and deadlines for the project to meet, the developer can spend his design and permitting money, but if he doesn't start construction you can terminate the JV.

Just make extra payments on your mtg with the same Extra money you would pay back your heloc with.

The city does not have any duplex related permits.

Maybe market it as you be willing to let tenants rent extra room on Airbnb?

Obviously, even just based on the 2015 data, the price + taxes (not including renovations needed, etc.) make this property impossible to cash flow if the town ever clamped down on the extra 4 illegal units.

Stop trying to chase a few extra dollars per mo by putting significant money at risk....