The Island was on a roll Friday night at the Viva La Vineyard casino night at Outerland sponsored by the Island Affordable Housing Trust.

Money was raised for an Island family needing a few thousand dollars to get over the top of their mortgage needs, a hard-working single mom won the $500 Hinckley’s gift certificate for most chips, and 125 Islanders got dinner and two and a half hours of nonstop music from drummer Jerry Bennett and his Sultans of Swing.

A great night out for working people and high rollers was the plan, said Patrick Manning, executive director of the trust. “We worked hard to provide a reasonably priced event. We are a fundraiser, but we also educate about Island housing needs, and everyone who sees the possibility for themselves or friends and family is important.

“Year-round residents, summer people, green advocates and organizations such as churches are all part of the housing problem solution,” he said, adding that more affordable shoulder season events are planned, as well as off-Island fundraisers to complement the second edition of last summer’s mammoth telethon on Plum TV.

The venue was transformed by the trust’s volunteers and staff into a psuedo casino, with a glittery archway entrance, wall hangings and general glitz around roulette, blackjack and craps tables on both levels. The atmosphere was created by Annie Bradshaw, Jeremy Bradshaw, Dick Metzger, Maeve Sheehan, Victoria Haeselbarth, Philippe Jordi and development director Guinevere Cramer.

The audience also was part of the performance, with a Kenny Rogers look alike (a la The Gambler), vampy dresses, a smattering of tuxes and some Roaring 20s looks, including West Tisbury’s Caroline Flanders with a Clara Bow do and Plum’s Gwyn McAllister in a sequined red flapper shimmy dress.

The Sultans pulled out all the stops. The band filmed the event for a promotional video, featuring vocals by Joanne Cassidy, Ada Dyer, Jennifer Keaney, new vocalist Ellen O’Brien, Jeffrey Thomas, Alvin Roberts and Felicia Taylor. The Sultans also featured two Laugh In-esque dancers, Australian Katy Bloom, wife of trumpeter Eric Bloom and an Australian friend of hers.

The gaiety had a sense of purpose for attendees. The crowd included Fran and Bob Clay, quiet and constant Island benefactors, and Chris Rasmussen, taking a break from busily building her own Habitat for Humanity home to support others in search of affordable housing. Tracy Eide, a bookkeeper and single mom, knew the event was a financial stretch but came anyway because she’s familiar with the Vineyard shuffle. “Finding affordable housing on the Island is so difficult,” she said.

Ms. Cramer, director of development for the trust and architect of its $500,000 summer telethon, is keenly aware of struggling to afford housing. She and her husband purchased a home in Oaks Bluffs and work multiple jobs to afford it. “I want my kids, when I have them, to grow up in a real community and I want them to know kids whose families have been here for generations,” she said.

Volunteer staff included croupiers and dealers Natasha Taylor. John Stabile, Bill Seaborne, Amy Houghton. Bob Wheeler, Steve Berlucchi, Graham Houghton, Harvey Beth, Mary O’Doherty, Phil Combra, Lynn Macumber, Richard Leonard, a stoic Kevan Nichols and Steve Jordan. David Vigneault and Matthew Cramer were the unused bouncers who looked the part. Terri Keech and Susie Himel collected the cash with ticket-takers Maeve Sheehan and Susan Vail. Gerry Stabile photographed the event.

Mr. Manning, the evening’s master of ceremonies, explained that “affordable housing is a three-legged stool: [the trust does] fundraising and awareness and education; the Dukes County Housing Authority provides rental housing; and we work with groups like Habitat to provide opportunities — and we provide counsel and advice to towns or any organization that needs it.”

To date, 38 affordable housing units have been created of an estimated 500 needed, he said.