This is somewhat of a unique property and trying to figure out if this requires a commercial appraisal or residential appraisal. 

You will have some unique headwinds right now, but certainly doable!

Even rented together, that is a unique feature that will help you stand out amongst other listings.

Taking into account they will be staying at your property, will only do the ceremony there and me not being an expert on Florida but talking some colleagues that have venues in Florida about $250 to $400, not including the Airbnb stay.If you did the reception, $1750 would be a fair price, not including the Airbnb stay taking into consideration the additional insurance you may need to protect yourself as others have mentioned and you are not providing any of the decorations or labor but I am sure your cleaners would have to be extra thorough in getting the property ready for your next guest. 

.- Each of the units are unique (it's a monster house, with two additions and also a detached building). - Both the exterior and interior need extensive repair and reno, probably full gut rehab for most units.- The electricals will need to be separated and individually metered - is it possible to run new lines separately while gutting each unit one by one?  

The upstairs of the original home is a spacious loft/studio apartment with lots of unique woodwork.2.

SF deals are individual and unique and hence underwriting a PMI type policy would (likely) be cost prohibitive, especially as many of these deals are lower balance loan limits.

I would also use decorative gravel around the house.

It's true that the well known vacation rental communities (Championsgate, Windsor at Westside, et al) have higher HOAs but they also have extensive amenities which will drive higher rates for a well-themed and decorated home.

I eventually learned unique efficiencies that really helped me out as a landlord.You see, a property manager cannot be as creative as a self-managing landlord because they are constrained by company policy and what the owners want.