Location, Location, Location.
The comments made so far paint a reasonably accurate picture of the FF ticket market since St. Louis '07. Comfortably filled NHL Arenas; but not really a tough ticket. The secondary market has been an attractive option. Tickets at face value or below have been fairly easy to come by. Often seat locations are better than what's available in the lottery/selection process.
HOWEVER: We're talking Boston. Boston '98 was a pretty tough ticket. At least up front, Boston '04 reigns as the toughest FF ticket in the lottery era. And the tournament hasn't been back since. There's at least some pent-up demand. So for those with any priority points at all, I recommend locking in your seats this Fall.
I'm fully aware of the big picture. Current demand for FF ducats is significantly less than the peak years. Short version of a long story: The speculators and scalpers are basically gone. Non-traditional sites took away much of their customer base; higher face values squeezed profit margins. Supply and demand have settled into a comfortable equilibrium.
But again, we're back in Boston. A modest sellers' market may make an encore appearance.