At Code for America, a great deal of thought goes into what's possible with apps. But I miss the reflection which came with OLPC, the question of where programmers come from in the first place.
It's actually super-relevant to our work in cities, because not every city fosters a programming community. Most cities have a dedicated and hard-working IT department, but local coders provide the lifeline for new ideas and skills, an unofficial partner in apps and hackathons. Think of RAP Ceibal's work in Uruguay.
My city team's strategy focused on a local university. I made a few appearances at MUGTUG, a late-night CS meeting where students share projects centered around Google APIs. In the future, we hope to drive this group to develop a musical map of the city ( something technical, but not overwhelming ). But for the most part, CS students aren't taught languages of the web. It's so odd - I mean, the world is web. But two weeks ago, a Berkeley grad student told me that she'd quit Codecademy, because her professor wants her to focus on Python.
My own experience? I like learning while working - the start-up way. This year I have completely overhauled how I make websites. Even maps!