I think there definitely IS a way to position for a big FA that year, but it would take Pierce opting out...renouncing the rest of the roster isn't a big deal really, as Perk/Powe/KG/Rondo and some rookie deal players is enough of a base if they were to bring in a Dwayne Wade into the mix. They'd likely have a deal in principle with Pierce to re-sign for mid-level after the renounce him, so he'd probably just sit around waiting to re-up. After that, the team can just fill the roster with vet minimum players and still be title worthy.
But, there are some steps before straight free agency:
1. Youth development: Rajon Rondo, Perkins, Powe, TA, Pruitt, and Bill Walker will have a say in what happens in 2010. People expect Rondo to be a star. If Walker, TA, Pruitt, or even Giddens start to show major flashes late this year and next season the team will adjust accordingly.
2. Trade/sign-and-trade: Depending on the aforementioned youth, Ray is a prime candidate for S&T after next season or possible trade anytime before then. He isn't going anywhere this year, but as that 2010 FA class gets closer, teams will be juiced about getting a 17 million dollar expiring deal - Boston is in good position here.
3. Pierce opts out - least likely and most complicated, but it IS possible. Even with the number of players the team would have to renounce, they'd still have a core group of 8 players or so and would have plenty of money to flesh the roster out with low-priced scrubs. If the team feels it has a shot at a superstar in his prime, they will work to get him.