@Jaron Walling It does not appear to be in a flood zone.

I'd expect something closer to $30/month.If your rent and reno numbers are good, and this isn't in a war zone, I bet you can cash flow $300+/month.

The seller won't release the P&L until we're under contract.When I plug in an estimated 7% for vacancy/concessions, the deal rocks, but I'm concerned that the current NOI (with high vacancy history) doesn't justify the price of the deal.In this type of situation is it reasonable to make an offer and then get the official numbers later, or is it a red flag that indicates the deal should be avoided?

For some reason, the list and department that handles zoned and improved upon properties are telling me they do not handle raw land and send me in circles. 

Hello fellow investorsTalk about getting out of your comfort zone!!

Orange county zoning does not allow Short term rentals.

Good Afternoon,A contractor may give direction but will not advise on something an engineers opinion is needed on such as a load bearing wall or structural item separating units.Secondly I would contact by phone or email (I recommend email) Tampa or Hillsborough Building and Zoning department and ask them.

While it may have been a little more expensive to refinish and patch in red oak flooring instead of tearing it out - it made a huge difference in the feel of this home. 

The other option I looked into is the Katy/ Cinco Ranch but what is not +$500k is in a flood zone.

That's a big red flag and a lawsuit waiting to happen if things go south.