NBA star Scottie Pippen (in a recurring role as the guys' landlord) joins the cast in an outing about Mike taking his brothers and Lindsay to the Bahamas. While there, Mike is wooed by Bahama sugar mama Nina; Harry has a go-round with the roulette wheel; can-do Billy goes condo; and ""elitist snob"" Lindsay has a fling with a cabana boy.

While Harry and Mike argue about meddling in love struck Billy's private life, their little brother puts his foot down and takes a big step on his own. So, it's up to the older Kuchaks to save their impetuous sibling from the mess he's gotten himself into.