I woke up one day and realized I needed to run all my deals in the same way a hotel manages all their properties.

On Oahu, for example, we have "resort zoned" areas that are mostly hotels and condotels, and there is a permitting process, different property taxes, etc. for real estate bought in those zones.

In addition to that, tax revenue from STRs tend to be significantly lower than that of their hotel competitors. 

I've never stayed in a hotel or short term rental where I couldn't control the temperature.

That said, deductible would likely be $500 or more so how many nights would they need to get a hotel for instance and what would it cost?

I don't know if you're aware but luxury hotel rooms are often super cheap in that country so I'm not sure how you'd compete and make any decent income.

Just curious what hotels do in these hurricane-prone areas. 

From $400-500k boutique hotels, to Lake or Riverfront RV parks for $1M+ to 300+ storage units for $2M these are not institutional asking prices (as are common in neighboring States.) 

You can check the zoning but if it's a commercial building that's an apartment complex or old hotel turned residential, you can do whatever and the city can't make you come under the permits they require for non-commercial STR properties.

Renting by the room is almost like running a Bed & Breakfast or hotel except for longer term stays which is why they often are not allowed in R-1 residential neighborhoods.