The Pirates' 40-man roster needs to be set by Sunday. The Pirates haven't had any October drama in over a decade, but the front office has outdone itself in creating November drama in recent years - the setting of the rosters has often disappointed people who care about the Pirates, but at least it has thrilled general managers in other cities.
Fortunately, there is unlikely to be a Rule 5 mess this year - Josh Sharpless will likely get taken if he's not protected, and so might Adam Boeve, Craig Stansberry or Mike Connolly, but none of those guys is nearly the prospect Chris Shelton was. Also, the Pirates have lots of dead wood on their roster right now, so they should have no problem clearing as many spaces as they need.
Anyway, here's a hot stove timeline, and here's WTM on the decisions the Pirates have to make.