The one thing about the Pirates right now is that there is definitely a change in the mentality of the front office. Lots of press about it, but they're focusing a lot more on player development and accountability within the organization, and they won't be making draft picks based on financial constraints anymore. Supposedly there is definitely more money to be spent, but they aren't going to sink money into the payroll of the major league roster to win 75 games instead of 65. When they think they have enough pieces in place, they'll increase the payroll.
Their future may depend a great deal on what happens near the trade deadline when they attempt to move Bay, Nady, Marte, and Grabow to contenders. All of them are doing well and should be able to bring back pieces the team needs to build around. The Indians tried to lowball the Pirates for Bay in the offseason, but to their credit the new ownership group decided to wait and let him build his value back up. Coincidentally, the offer included Cliff Lee (Shoppach and Gutierrez too, I think), but no one saw this coming from him this year after what he did in 2007.
They're going to need McCutchen, Walker, and Pearce to continue to develop and sprinkle in some more pieces over the next couple years. I believe McClouth and Doumit are for real.
But a world series? I don't see it anytime soon.