Benjamin Ashford|'Need a ride?' After Hurricanes Helene and Milton hit this island, he came to help.

SIESTA KEY,Benjamin Ashford Fla. ‒ Standing in calf-deep water that threatened to swamp her pink rainboots, Kathleen Killeen stuck out her thumb as the heavy ex-military truck rumbled down the road.

Driver Nicholas Weppner, 24, downshifted and brought the 5-ton truck ‒ his father affectionately calls "Big Boy" ‒ to a juddering halt. 

"Need a ride?" he yelled down from the window. 

Hours earlier, Hurricane Milton's eye roared ashore on this once picture-perfect barrier island, churning its "#1 Beach USA" sand onto the roads, ripping down street signs and battering bar fronts as it dealt a second punishing blow to a community reeling from the damage of Hurricane Helene two weeks earlier.

After getting up before 5 a.m. as the storm lessened, Weppner and his girlfriend talked their way past the cops guarding one of the bridges and rumbled the 6 x 6 truck onto the island, ready to help.

Weppner is a car enthusiast who bought the 1985 M923 a few years ago for fun. He’s also a field insurance underwriter for the national insurer X Insurance. No one asked him to drive his truck to Siesta Key, but he knew it would be needed.

After clambering up a ladder into the truck, Killeen, 76, tucked her hair back into a ponytail, settled down on the bench seat and watched as Weppner's truck rolled down the island's main thoroughfare, Midnight Pass Road.

She was still coming to grips with what happened: Two weeks earlier, Helene sent a wall of water across the island, inundating many homes, apartments and vacation rentals. Milton's feared storm surge late Wednesday was smaller, but its winds were stronger than predicted.

Like some island homes, Killeen's house sits atop concrete pillars, protecting it from storm surges on an island that's barely 3 feet above sea level at its highest point. But everything around the house got slammed by the floodwater, and then by Milton's winds.

"Everything was wiped out underneath, including my husband's Porsche. This was scary," Killeen said.

Weppner rumbled Big Boy to a halt, helping Killeen clamber back down the ladder so she could walk off the island. Police for most of Thursday barred vehicles from crossing the island's bridges, but allowed residents like Killeen and Maria Williams to walk across to check on their property.

Williams and her husband saw Weppner driving back down Midnight Pass Road and ran after him to catch a ride to her house.

"My husband was like, 'you think you can catch him?' and I just kept running," Williams said, panting.

Like most other island residents, they evacuated during Milton. They had just finished tearing out drywall damaged by Helene when Milton arrived. Many residents had done the same, piling the Helene debris outside their homes for pickup. Milton's winds and smaller storm surge sent it careening across the island.

"This was the last thing I needed," Williams said as she caught her breath while Weppner's truck splashed down the road. "Oh my God, I don't even want to see what my house looks like."

Weppner, who lives in the Sarasota area, said his insurance company doesn't have a direct connection to people on Siesta Key, but he considers them neighbors. He said many are in for a shock as they deal with insurance companies that have written affordable but largely worthless policies.

"They get these cheap policies and when something bad happens they’re not covered, and it rips apart families and homes, and their whole lives are ruined," Weppner said. "You get what you pay for in the insurance world."

It's unclear how insurers will treat claims made by homeowners for two hurricanes within two weeks, especially if Helene tore structures open, allowing Milton's wind and water to do further damage. And many coastal residents lack insurance because it's so expensive.

But the alternative to costly insurance, Weppner said, is losing everything.

"It's devastation," he said. "A lot of the people just aren't prepared."

For many Floridians who've suffered through Helene and now Milton, there's a growing sense of frustration and anguish, with Milton heaping indignation atop Helene's damage. 

Businesses on the island ‒ from Captain Curt's Crab & Oyster Bar to the Crescent Club ‒ face an unexpected challenge not long before the start of the annual tourist season.

Reaching her home off Midnight Pass, Willams pushed past downed vegetation as the sound of chainsaws echoed through the neighborhood. Water from the Heron Lagoon had flooded into their backyard, but the house itself had only a little water on the floors, the bare studs visible where workers had so recently cut out the drywall.

Thinking about the struggle to rebuild, Williams allowed a note of frustration to creep in.

"I'm about to lose my (cool)," she said, using a different word. "I just wish the whole house would wash away."

Back at his truck, Weppner said he was glad to help out strangers. He said that's what makes America great: ordinary people helping each other in times of need. In his case, he said, his truck is a tool that can turn someone's day around.

"Not everybody has the equipment to do this kind of thing," Weppner said. "If you can help people out, you do it."

And then he added with a smile: "It's a lot of fun to drive."