Area residents with Florida homes assess Hurricane Ian damage from afar

Thursday morning, she even thought it might be: Initial pictures of the outside of the home, taken by a neighbor, showed a modest amount of damage.

A crumpled roof. A collapsed carport.

“My mom, she’s so strong,” Jackie Middleton, of Waunakee, said Friday afternoon. “She was like, ‘It’s OK. It’s the outside. We’re going to be able to rebuild that.’”

Hope faded later Thursday, though, when the neighbor was able to get inside the home, where a damaged roof let rain pour in unimpeded.

“It’s just devastating,” Sandy Middleton said Friday, from the Castle Rock Lake campground where she stays each summer. “I don’t even know what to do when I get there. I can’t live in my house.”

When Ian blew across Florida on Wednesday as a Category 4 storm, Madison-area residents who own properties in the Sunshine State couldn’t do much more than watch, wait and hope.

It’s unclear precisely how many Wisconsinites own homes in Florida: The U.S. Census Bureau tracks second-home ownership, but not to that geographic specificity.

But long, cold winters tempt Northerners to travel south each year, and the Sunshine State is one of the most popular destinations.

As of 2018, between 20% and 30% of homes in the Fort Meyers region are their owners’ second homes, according to a National Association of Home Builders analysis of the 5-Year American Community Survey.

U.S. Sen. Ron Johnson, R-Oshkosh, has a home in Fort Myers. Former UW-Madison football coach and athletic director Barry Alvarez spends winter in Naples.

Tasha O’Malley lives in Sun Prairie with her husband, Brendan. Earlier this year, the couple also bought a house in St. Petersburg, Florida, they rent out as an Airbnb.

“We thought about driving down to board up the windows,” a 1,300-mile journey, she said.

But a Florida neighbor convinced the O’Malleys to stay put.

“My husband might get stuck, there’s bridges that could’ve closed and kept him off the mainland,” Tasha O’Malley said.

Their St. Petersburg home weathered the storm with just some yard debris and, for a few hours after the hurricane passed, a power outage.

Sheri St. Mari splits her time between Verona and Naples, selling real estate in both states.

St. Mari was in Naples this week when she learned about the impending hurricane. She texted her children in Wisconsin to ask if they wanted her to head north, but even before they replied, she was packed up and en route.

“I feel like a traitor because I left my neighbors there. That’s what happens when you (live in) multiple places,” St. Mari said. “But I had to come for my children. I had to respect that there’s a mandatory evacuation.”

Sandy Middleton plans to return to Florida in three weeks, after the water in her Castle Rock campground gets turned off Oct. 15.

So far, she’s been unable to reach her insurer, and her policy documents are in Florida.

She doesn’t know where she’ll stay. She doesn’t know how she’ll clean up her property. She doesn’t know what can be salvaged.

“It’s just kind of overwhelming, and everyone asks a lot of questions, and I’d like to take 24 hours to not talk about it,” she said.

But, she said, reality won’t wait.