Either this team starts to win now (via spending some dough, most likely), or there isn't a whole lot to hope for in the coming years. If they bring back pretty much the same roster as last season (not necessarily in name, but in "questionably shitty player"-for-"questionably shitty player" fashion), this team isn't going to do a whole lot, attendance will continue to suffer, and the freedom brought by the expiration of the likes of the Buehrle/Jackson deals will be a moot point, because JR more than likely won't sink huge money into rebuilding a team with shaky attendance.
Then again, I could be wrong, and perhaps there is one or even two more seasons with the window of possibility of this team spending big money to get back into contention remaining open, but I don't think it likely. Could they just want to tread water and hope to land someone like Prince Fielder after 2011? Maybe, but if this team is struggling (both in terms of attendance and the standings) on into 2011 there is a good chance the organization gets stuck in a cycle of shittiness: shitty team breeds shitty attendance breeds shitty revenue breeds shitty budgets.