I got maybe $20-30K of fence /tree damage at House #3 From Laura, that I am waiting for better contractor pricing to address. This house is 100 miles inland, so its not really and only a matter of living on the water. 2020 just was a bitch of hurricane season. Let's hope for better next year.
This place was an old homestead built by my great grandfather in 1919. Most sad was that many 100+ y.o old oaks and pines were lost, that surivied 1925, Audrey in 1957, and Rita in 2005.
Well, shoreward of that place, I'd wager there used to be waterman's hangouts, and waterfront places that were either summer cottages, cabins, and few year round residents. Those who were where I grew up either farmed, fished, or both to make their relatively meager ends meet. Now, wealthy people have 'discovered' the waterfront, and even a view of the water is a selling point for houses that dwarf those older edifices.
In any era, size costs money but the reevaluation of real estate (which caused many to be taxed off their land) means a sugar shack near the beach is worth more than a decent house inland.
No matter how you slice it, the damage from any given storm is going to be greater in monetary terms because of the valuation of the properties today, and the tendency to go top shelf on accommodations. Sixty years ago, having a fridge that worked was key, not what color it was or whether it was restaurant grade and stainless, and no one had granite countertops. That's just a small example, like having a flush toilet, central heat, and other relative luxuries. Greater density of population contributes: there is more for any given storm to hit.
Let the storm track over you, it's more severe. More than one, or a wet year prior to getting hit, and trees are going to come down. That's the luck of the draw.
The house I grew up in (3 br, 1 bath) was valued at 20K (new!) including the two acres it sat on, two sides of that waterfront. That was 1960. Now, the taxes on the place are over 30K a year because of reassessments (with well water, septic, not city water, and a 1/2 mile gravel drive with no state maintenance).