I love the Pirates and their is some good young talent. McCutchen is pretty awesome. Milledge consistently underperforms every stop in his career so far. He was once one of the most sought after prospects in baseball. All in all though, I think the guys in the field are decent enough to be an above .500 squad. Pedro Alvarez should be a good call up from the minors, this season I hope.
The top of the pitching rotation (Duke, Maholm) are homegrown draft picks (20th round for Duke and 1st for Maholm) that really are more suited for 4 spot in a rotation. These are not the "aces" that a good club has. I know the baseball draft is a lot like a crap shoot and the development of baseball players is such a LONG process, but they have been drafting pitchers high up in drafts for the past 6 years and there isn't a lot to show for it.
The front office is starting to make moves I like. I think there is a serious coaching problem in both the majors and in the farm system though.