If it is "an old house", it has done pretty good performing in a hurricane area so far.

What is the roof pitch?

Big question; little info.

The wind insurance cost is Astronomical- $6,000 a year - and these houses seem to need new roofs every time a major storm comes by. For comparison, my current house has a tiled hip roof and had gone through 2 storms with 0 issues. If it’s doable a hip roof would be preferable, but if terribly complex we can just do the best gable we can.

Regarding pitch - I don’t know, since I don’t have a specific house in mind - I would say the average 1/4 or 1/3.

I think you'll be best served by contacting a local remodeler. I also recommend you contact your insurance agent to see how much the insurance premium would be reduced after you make the modifications.

Just curious, have you been quoted what your "wind insurance" premium will be after switching to a hip roof?

@Jrb451 I have reached out to my agent but have not heard back yet.

If the roof slope is low and the end gable well attached at the apex (this is easy to achieve), converting it to a hip roof is unlikely to make a practical difference.

A major consideration is whether or not the new hip needs support from below and how difficult that support would be to build.

Another consideration is the shape of the roof plan. Is it a simple rectangle or more complex?

What will the roofing be? How is the roof framing tied to the walls and the walls to the foundation?

Building height is a factor too.

Older house construction in FL did not do well with anchoring the walls to the floor, or the roof to the walls, the roof decking the the framing, etc.

In the Wind Mitigation Reports that the insurers use they are documenting approved steel connections at all these critical junctions. That is, they must be able to see and photograph these connections or you get no credit for them.

To retrofit with these fasteners, parts of the walls and roof decking often need to be removed to get proper access.

Often older concrete block walls were not properly filled with concrete.

And, in my opinion, all roof decks should be covered with a waterproof/resistant peel and stick membrane. It helps prevent water intrusion when the outer roofing layer blows away.

@ulisdone, this is exactly the kind of info I need. I agree with you regarding the waterproofing. That is terrifying about the blocks not being filled. Is that even something you can find out during an inspection? I imagine you’d only see it once you tear everything down. Although I guess if the home was in Andrew’s path and survived the walls must have been properly built 🥴

For the filling of the cores of CMU to be structurally effective the cores should be filled with grout with vertical rebars as specified by an engineer. The engineer will determine if inspection holes are required at the bottom of the filled cores. The vertical rebar should lap the bars from the foundation.