Does living in an age of skepticism help or hinder?

From an interview with Tim Keller in the September/October 2010 issue of Modern Reformation (emphasis mine):

In some ways, belief in an age of skepticism is a Manhattan perspective, because I don't think you can necessarily look at the entire country and say we live in a skeptical place, that belief in the orthodox Christian faith in such a skeptical culture is difficult, or that this is what it takes. But I think you can say that Manhattan is a skeptical culture, so I was really talking about those center city / university areas where people are very skeptical about Christianity. When I arrived in Manhattan twenty years ago, I was expecting evangelism to be more difficult. It actually has not been - humanly speaking - more difficult, because people are so overtly skeptical; whereas other places I've lieved, such as Pennsylvania and Virginia, there was the veneer of civil religion and it was harder to get traction with people.

The original question actually refers to the U.S. context, whereas I'd say that the Canadian one (and even more so that of Canadian universities) is closer to the Manhattan perspective that he speaks of.