I don’t know the laws there, but for sure the only fault will be your own, who in this modern world pays for large upfront?

It's a great canvas to improve upon --I suggest the following to make it more modern & appealing without needing to invest a lot in the exterior or change the structure:Coat of paint to make it more modern I suggest keeping it simple with white tone exterior with black accents (on the railing, shutters, trim and sconces) https://people.hgtv.com/professionals/prairie/mode...Add shutters on both sides Update the sconces to something a little larger and more modern to add visual interest and take up some of the blank spaceAdd simple landscaping on either side to introduce greenery against the simple color scheme of the homeBest of luck with this!

The location, views, and buildings are fantastic - just needed a bit of modernizing and the right team to market it to its full potential.

None of the national carriers (travelers, Alstate, American Modern, or Statefarm) insure STR or property in FL... very odd. 

A unique mix of history and modernity!

I got several quotes from big companies such as Allstate, State Farm, and American Modern.

Hi Yiftach,If I were considering this, I'd come at it kind of backwards.Meaning I'd come up with a per door max I could spend in rehab and still hit my intended numbers.I'd also take into account the length of time each unit will be down (best and worst case scenario) and figure that into the numbers.Then I'd come up with a "Package" (how I want each unit to be to make it "Competitively rentable"), appliances, floor covering, faucets, doors, hardware, HVAC, modern required electric, etc... and Hard price that package for each unit, estimating the price increase over time as all units will not be done day one.Then get bids on the labor required to do the work.I'd split labor from parts so to speak, to control the parts purchases as much as possible because I know exactly what I want down to the part number.

yes, some version of this is found in every modern day mortgage, however, there are documented and regulatory exceptions for transferring title to property and NOT triggering Due on Sale....especially when the purpose of the transfer is to entities for the sake of estate planning/asset protection.

The outcome was a beautiful modern duplex that was easily rented.

A good sign of no insulation is lathe walls which are a rough texture wall unlike modern drywall.If the walls are not insulated you will have to look at the options and the cost involved to see if it will be cost effective.