Joe, Helen, Brian, and Casey are fed up with their living arrangements, and Joe's "big board"; however, Felix the Contractor says the sinkhole on Joe and Helen's plot isn't the only delay in building their new house. Joe shows Helen the house of their dreams. But what to do with their poured foundation? In the meantime, Antonio gets $1000 tax refund and decides he is going to spend it all on himself. Unfortunately, a broken tooth leads to a series of unfortunate events that whittles his check down. It all ends in fire and chaos, reminiscent of... last year.
Brian and Casey burn down Helen's house; Joe and Helen burn down Brian's house. This is too much of a coincidence for the insurance company. Joe, Brian, Helen, and Casey must sweat it out with the insurance adjuster before Antonio shows her passion can ignite a flame.
Antonio works a suicide hotline one night and finds himself on a date with a depressed caller. When she turns out to be gorgeous he wonders how long until he gets dumped. Helen has to compete with a sandwhich vendor cart.
It's Halloween and everybody wants to enjoy it and go to parties. A guy shows up and buys a ticket. Joe and Brian don't want to fly him because they have plans. The guy gets a call from his wife, who had earlier dumped him. He says that he's a medical courier and he is carrying the gift of life. Joe and Brian convince him to go to his wife and he leaves his cooler behind. They look inside and see a canister that says Nelson's heart. They assume it's a heart for a transplant. So they try to find out where it goes.
Casey encourages Brian to use his insurance money to open a martini bar. Things go awry when the first customer through the door slips and falls. Brian's problems are compounded when he learns Casey never got insurance. Roy and Faye hunt for ET's.
Cord's first act as the new President of Sandpiper is to hold a meeting, informing everyone they need a "big idea". Joe tries to get everyone to see there is no "Big Idea". But it turns out there is. Little does Roy know that he would be responsible for the "Big Idea", mentioning to Cord that the charter business is the one he hasn't been able to crack. So after contacting friend of his in the music business, the "Big Idea" pays off when Sandpiper becomes the charter for the singing sensation the Todds (a TV version of the Judds), that is until a feud breaks out and ...
When Cord chickens out on delivering a presentation before his father's board of directors, Joe and Brian must deliver it. Meanwhile, hanging out in the men's room, Helen's learns a nasty secret: Cord was expected to fail at Sandpiper for the tax write-off.
Another odd Christmas falls on Nantucket, as Antonio drives a nun around in search of a vision she saw in a dream. While Joe plays reluctant host to feuding brothers Lou and Harry, a little last minute shopping ends up trapping Fay, Helen and Casey.
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. A con-man robs them of their money, Helen is forced to compete in a drag queen contest. A bad back leaves Joe in the house alone with a talkative Antonio.
Kicked out by Joe and Helen, Brian and Casey move into a new home with the help of a new roommate Antonio who actually lives with his girlfriend. Things suddenly become crowded when Antonio is dumped and has to move back home. Joe and Helen's nudism has them threatened with blackmail when the neighbor kids snap photos of them.
Joe makes a music room in the attic for Helen. He moves a piece of luggage out for Brian, who discovers a secret note from their deceased father and key for a lock box. The duo set out on another finder's keepers quest, just like they did eight years earlier. They enlist Faye, Antonio and Casey on their quest, which takes them to Boston, New York, and eventually back to Nantucket, only to find another suitcase in the airport locker, right next to the one from eight years before. Helen plays for another symphony and gets turned down again.
This time the suitcase actually contains money - a lot of money. Brian and Joe fight over what to do with the money, Joe always practical, Brian always impulsive, and go their separate ways. This leaves Fay wondering if she will still have a job, but instead Joe offers her 5% of the company for her loyalty. Helen hears back from the conductor in her interview and is invited to study with him in Vienna, but Joe doesn't want to leave Sandpiper. But when he learns of Helen's amazing opportunity he makes the ultimate sacrifice and finally actually agrees to sell Sandpiper...