I think the team is FINALLY headed in the right direction. You basically have to choose if you want to develop players or go about building your team through free agency. For years, the Pirates did neither, they signed economical draft pics and made trades for guys to just fill spots (anybody remember Bobby Hill?). They have finally started to build a pretty solid farm system and got rid of nothing more than role players to do it. Combine that with a strong draft and the Bucs should have a Top 5 farm system next year.
Next year, if they aren't in contention at the break, they will HAVE to start trading some more pieces (Duke, Doumit), if they are in it at the break, I really think you will see them use some of their pieces to go out and get some help...