The interior was outdated, the landscaping was overgrown, and several deferred maintenance issues were apparent.

The issue I have seen with these types of properties is they could have two valuations - the value of the real estate which the structures will have little value and you have the land the other is as an operating business just like a bed and breakfast would have - real estate has value but it operates a business now you mention 12k / month but if someone also has to manage the property what is that worth and what would someone pay to manage a property like this?

Yes the biggest issue was they grew way too fast and he set up an entire servicing company to handle all of their deals.

I sat in on a lot of the meetings with owners/city and it seems for the most part to me, the city is just not interesting in AirBnB and as an investor, that's not a good place to be or be right.There will always be probably a few people who skirt the law or think they have a good workaround, but often catch 22. 

Furnished Finder is what we use to list all of our mid-terms and don't typically have any issues finding tenants. 

I contacted Zillow about this issue but received no response.

They appear to have run into liquidity and cash flow issues currently and worst of all have gone dark and not shared any of the requested financial information.

Now, with taxes, insurance, and interest higher and rents not keeping up with property values, most investors are putting more down to get the properties above a 1.0X DSCR. 80% is acceptable, but the issue is getting the property to cash flow at the higher amount. 

Quote from @Daniel Reed: @Jonathan Greene So, are you suggesting that this issue is indeed driving investors away from Florida?

The inspector should be thorough and telling you any issues.