Definitely not confusing the size of Scott's management team. But the fact is he has a personal assistant, a manager, and when on the road a tour manager. Whether or not one person overlaps these responsibilities or if there is a small group, the roles certainly exist. And part of those job descriptions is to coordinate his schedule and juggle contracted responsibilities.
While yes, ideally, Scott should be aware of what is attached to his name and his responsibility, I think it might be a bit out of touch to think that remembering to fulfill the Pledge autograph items is near the front of Scott's mind.
Either they set a couple of dates for Scott to get to a location and sign a bunch of stuff, or they delivered crap to Scott's house and told him to sign by x date. Either way, they're late.
The lateness of non-autographed items as well seems more frustrating. Not sure you can give any excuse why a standard CD or t-shirt isn't ready. Just poor planning or poor execution.