Fraser Speirs, Mac software developer at ConnectedFlow.com has started a blog called The iPad Project in which he describes the ups and downs of rolling out a whole pile of iPads in his school in Scotland.
It is a work in progress daily blog currently up to day twelve and is well worth a read if you are at all involved in ( or will be in the future ) deploying iPads or iPhones into any moderate sized organisation. Certainly the information about how they intend to tackle the issue of installation of paid for applications was of interest to me.