We are using one Mac as the iPad master for syncing and updates, with our own iTunes account, so we pay for everything. But next year, when we go 1:1 with the iPads, we will most likely have students use their own iTunes accounts for purchasing Apps. We might give them an iTunes gift card for the Apps that we require, and then they can pay for whatever else they want on it.
We can image a class set from the master Mac according to a teacher's choices. But all of this maintenance has required the hire of an additional staff member, who comes in the afternoons and evenings, and goes around taking care of power and syncing needs. We've only got about 400 units, and he's already putting in 40 hours a week. So, you can see that maintaining control of the machines, just like laptops/desktops, is going to require a lot of work. And more importantly, Apple didn't design the iPad for multiple users, and they have no intention of changing that; this means the only real 1:1 solution is student sets (i.e., every student carries their own) rather than class sets. Believe me, we have class sets now, and they're a pain. We're pretty set on going with student sets for our 1:1 launch next year.
I have to disagree with the previous post concerning the Configuration Utility: it offers the world, and leaves you with dirt. It really doesn't do much. Management software running in the background is direly needed, but at this point, the limited multi-tasking of the new iOS will not allow for it--believe me, I've been negotiating with vendors who are dying to get a crack at this market. Their products are ready to be tested but the current iOS won't allow for them to run. Some people on this forum have hinted that the RAM on the first iPads is insufficient--don't know. We'll have to wait and see what develops.
Keep fighting for iPads in your district. At my school, we've already seen great benefits over laptops and desktops, despite the troubles of working out the bugs of a new technology.