And surely they'll have to bump it again or introduce a new level; they're already back down to 800 remaining (currently out of 10,000), still with 29 days to go. The $99 pledge level wasn't even in there initially; I think they were expecting the bulk of their pledges to come from low-end pledges where people reserve a username. They're also out of etched boxes ($225 level) and even most of the developer specials ($700) are gone.
Considering that at first they had just enough slots to reach their goal I think they are managing the launch to maximize unit sales and hype.
What I am surprised about is that they did not raise the price above $99 with the second top up (20,000 @ $99). Thus $99 must not be a below cost loss leader. My guess is that they will offer as many $99 units as possible. Their balancing act is to offer an unbounded number of units while maintaining the air of exclusivity. Offer too many units at one time and people might thing they are missing their sales target.
With this much hype and sales they should have decent leverage with developers. I got the impression that a few developers they talked to were on the fence. Their first update could be interesting.