The White Sox organization is hesitant to use the term "rebuild" because the after-shock of the White Flag Trade still remains after all these years. Otherwise I don't know if there is a philisophical dilemma within the organization. If money is being made, what dilemma can there be?
I do think the team realizes it can't go through what it did in the late '90's. They can't have interest that low and expect to survive. So the organization has to show it has some interest in winning. They realize the economy is still not good and people are not going to shell out money to see a team win 80-85 games and finish out of the playoffs - again. At least the parking cost is down.
Other than that, I obviously don't know what goes on behind closed doors. I still don't think this ownership understands fans and, by this time, I don't think they care to. But they may have what they think is a solid long-range plan, and they may feel it is working. It just doesn't appear to be working now. Before we know it, it will be 10 years since the World Series. And that will pose a problem for the team, one much more real that philosohical in nature.