Joe and Helen burn Brian's house down and he expects to get a big check like they did. But the insurance investigator thinks Joe, Helen, Brian and Casey are conspiring to commit insurance fraud. Antonio manages to woo the woman and get a room at the Century Inn, where she leaves an unextinguished cigarette lying around.
Joe and Helen meet the next-door neighbors, Steve and Barbara, but what starts out as pleasant soon turns disturbing when Steve asks for $5000 to cover his gambling debts. Becoming increasingly paranoid after a fight, Joe and Helen decide to try and make amends, only to find out their new neighbors are only on the island for the month. Meanwhile, Antonio receives his Uncle Bernardo's personal affects after he dies, including a set of perfume scented love letters appearantly from Bernardo to a c
Brian's vow to find a deeper, more meaningful relationship is tested by beautiful but dumb Dani. Meanwhile, Joe tries to deal with the fact that one of his best friends didn't invite him to his wedding.
As a furious storm rages outside, Joe and Helen stop by the "Singles Mingle" to drop off Brian's wallet, intent on leaving as soon as possible to begin celebrating the first anniversary of their wedding. But news soon comes that the roads are closed due to high water and everyone is trapped. Not wanting to let everyone know they are married, for fear of their reaction, Joe asks Helen to be his bride again. Meanwhile, Fay, Roy and Casey mingle, while Antonio is offered his money back and asked t
Antonio volunteers to man the Nantucket Suicide Hotline. It soon pays off for him when he scores a date with a caller he helped. When they meet he can't believe his eyes or his luck and keeps waiting for the other shoe to drop—for her to dump him.
On Halloween, the gang convinces a man who is separated from his wife to stop being so focused on work and spend time with her. Little do they realize that he is a medical courier, and he left a cooler with one of his deliveries at the airport.
Casey suggests that Brian uses his insurance check to open a martini bar with her as the manager. However, when a customer (Stuttering John) suffers an accident on Brian's property, Casey says she neglected to have Brian's bar insured.
A financial crisis forces Joe to seek out an investor. When businessman Edgar Clayton comes to the island, Joe thinks it's his lucky day. But Clayton informs Joe he doesn't invest in businesses, he buys them. With no other choice, Joe sells. Joe and Brian are glad that with Clayton's backing they got their plane out of repossession and are up and running, until Clayton says now his slacker son Cord is the new president of Sandpiper.
The first act that new Sandpiper president Cord Clayton does is hold a meeting telling everyone they need a big idea. After learning that Roy cannot break into the market of charter flights, Cord proposes making Sandpiper an exclusive charter service, and has Joe and Brian fly a pair of bickering mother-daughter country music singers. When the tour fails, Cord tries fleeing, only for Joe and Helen to tell him he must be a man and face his father at a business meeting in New York.
Cord returns but becomes nervous during a presentation before his father's board of directors and leaves, leaving Joe and Brian to continue. Helen overhears one of Clayton's young hotshots saying that he recommended Cord for the presidency of Sandpiper in order for him to run Sandpiper into the ground, which Clayton could use as a tax write off. Clayton takes the news badly but, at Cord's behest, allows Joe to run Sandpiper to him and agrees to stay on as a silent investor.
Another odd Christmas hits Nantucket as Antonio drives a nun around the island who's in search of a vision she saw in a dream, Joe and Brian try to defuse a long-standing feud between two elderly brothers, and Fay, Helen and Casey get trapped in the basement of the department store where Casey works.
Roy falls in love with talk show host Mary Pat Lee (Caroline Aaron), but discovers she's using information he gave her to ambush Joe and Helen on her show. Subplot: Brian pays Casey to run errands for him.
Joe and Helen deal with a crooked vacuum cleaner salesman who charges them for a vacuum cleaner that had an eternal guarantee. Subplot: Brian comes up with a scheme to date Roy's niece.
Joe and Brian return home after vacationing in Las Vegas, during which Joe gets food poisoning after eating at a cheap casino breakfast buffet. When the flight's pilots also get food poisoning, Brian lands the plane safely and is hailed by the media as the "Angel of Flight 28". Brian's newfound fame is taking up all his time and overloading Joe at Sandpiper. Cameo appearance by Steve Young playing himself as one of Flight 28's passengers.
Fay holds a yard sale to help clear all of the clutter from her house. After selling goods that belonged to her three late husbands, Fay begins to be visited by their ghosts. However, Fay is also asked out by a man she met at the yard sale who tells her he values the memories of his relatives more so than the gifts they gave him.
Brian and Helen's trip to New York to see "Rent" turns into a nightmare when the theatre refuses to transfer the tickets from Helen's benefactor to her. Even worse, a con-man robs them of their money and Helen is forced to compete in a drag queen contest in order to get the money to get home. Meanwhile, a bad back leaves Joe in the house alone with a suddenly talkative Antonio.
Brian and Casey are kicked out of Joe and Helen's place, so they rent a house of their own with help from Antonio as they know he's spending all his time at his new girlfriend's house and won't be there. When Antonio and his girlfriend break up, however, they find themselves all living together. Subplot: Helen and Joe are blackmailed by some teenagers who have pictures of them doing various things around their house in the nude. Guest Starring Sibel Ergener.
Brian falls for someone after reading love letters mistakenly sent to the old occupant of the house. Antonio installs a home security system for Joe and Helen.
When Fay goes on vacation, the Hacketts hire a beautiful woman to fill in at the counter. Brian finds her distressingly distracting, while Joe and Helen have uneasy dreams about her. Meanwhile, Casey helps Antonio get a job at the department store, only to see him promoted ahead of her.
Roy invites Joe and Helen over to his house on an important night for him: the introduction of his girlfriend to his mother. But when he's dumped before the fateful evening, Helen reluctantly fills in. Meanwhile, Brian passes on his cold to Casey before her big date.
Brian's surprised to find out his girlfriend Emily Palmer (Shannon Tweed), has son is in college, named Shawn (Christopher Wiehl). Further complications happen when Casey starts dating Shawn. Joe and Roy try to overcome a fear of the circus. Rebecca Schull does not appear in the episode.
Joe enters a boxing tournament to beat an old rival. Things turn unusual when the rival is injured and the replacement contender turns out to be Brian.
To cheer up Helen, Joe restores her old cello. While Helen is busy rediscovering her old passion, Joe and Brian discover that the ages-old treasure hunt they undertook when their father died isn't over yet. They and the rest of the gang are led all over New England, only to wind up back at the airport and discover $250,000 in an old suitcase in an airport locker.
Joe and Brian are divided over their new-found inheritance: Joe wants to expand the business, and Brian wants to use the money to leave Nantucket and the tedium of his job. Joe's agony over the dissolving of the partnership is further complicated when he learns of Helen's earth shaking news: she's been invited to study cello in Vienna with the world's greatest cellist. Joe is prepared to sacrifice Sandpiper to help Helen finally live her dream, but it is Brian who makes the final sacrifice by po