Dynamic enterprisers Will and Grace begin a new business venture as they buy old apartments to refurbish and re-sell for a tidy profit. When budding ""student nurse"" Jack bumps into his former acting mentor Zandra, the pair of entrepreneurs finds their first project apartment. Meanwhile, Karen renews her romance with Lyle Finster, but the couple's bliss is interrupted by an unfortunate houseguest when Lorraine moves in.

Enjoying the success of their new business venture, entrepreneurs Will and Grace help their apartment buyers Jack and Stuart settle into their new life under one roof. However, when Grace receives a higher offer on the apartment, the ""friendly flippers"" attempt to break up the happy couple by encouraging Jack's cold feet as they see a chance to make a quick buck. Meanwhile, Karen demands that Lyle finally discipline his unruly daughter Lorraine, nearly shattering the couple's budding romance.

Opting to forgo a picturesque fall wedding to elope in Las Vegas, Karen hops a plane to ""Sin City"" with fiance Lyle and faithful friends Will and Jack but when she bumps into vacationing superstar Jennifer Lopez, she asks J-Lo to sing at the ceremony. Meanwhile, Leo returns from Cambodia to meet up with Grace at the wedding, but their reunion is delayed by a freak design accident.

Opting to forego a picturesque fall wedding and elope in Las Vegas, Karen hops a plane to ""Sin City"" with fiance Lyle and faithful friends Will and Jack. After arriving, they bump into superstar Jennifer Lopez who is vacationing and agrees on behalf of Rosario to sing at the ceremony. Meanwhile, Leo returns from Cambodia to meet up with Grace at the wedding, but their reunion is delayed by a freak design accident.