Listening to Mark Hammond's talk, Snake Charming the Dragon, is helping me assemble a better picture of Python's future role.
Generic GUI development will inherit from browser-based tools, such as CSS, plugins, various XMLs such as XUL.
Regarding OLPC: Uruguay and Peru (Arahay) are among the early adopters, also Birmingham, Alabama. The software development process still has a ways to go. Ivan Krstić is the man on the front lines here, literally risking his neck to get XOs in the field.
Ian has been generous in sharing his talents, having me go through a recording of my talk on his iTouch while penciling in filenames on a time line -- a first step in his video post production process.