At the San Francisco OLPC Summit, Bernie Innocenti was interviewed on his experience with One Laptop Per Child. It's a great video because Bernie is such a dedicated volunteer and his enthusiasm for One Laptop Per Child is palatable and he has such experience. Starting at around 2 minutes into the video, he gives great perspective on OLPC challenges and successes, and the maturation process deployments go through.

He also gives a radical piece of advice - don't support deployments. As in don't do too much to help the local deployment once its going, as too much help can lead to dependence, but force them to pick up all aspects of local support as soon as possible.