I would be interesting to know what mistakes made in North America and how they were addressed.

The major mistake was to assume that the most important use of the net was to distribute content from a relatively small set of sources out to the masses, and that the masses would pay for the privilege. In fact, people put a much higher value on one-to-one or one-to-few communication, and the number of content providers that successfully sell information can be counted on your fingers.

If you look at the history of web portals, early on they tried to present collections of exclusive content, all failing miserably except for a handful like the Wall Street Journal which already had vast amounts of high-quality proprietary material. The most successful portal I know, My Yahoo, offers its own content but also permits you to integrate any other source that has an RSS feed, which I think most users do. On my My Yahoo page, it's about 1/3 Yahoo's content, 2/3 from other sources.

On the other hand, putting existing off-line content on the net has often been very successful. Governments have put everything from tax forms to departmental phone books on-line, which is great. If you are worried about content, I would suggest concentrating on getting existing off-line content onto the web, rather than trying to generate new material. Don't expect the users to pay for it, so the first place to look for funding is from savings on material that would otherwise have to be distributed by more expensive means, and material that is directly of high value to users, e.g., commodity prices to farmers.

Also, for anything that has multiple chunks of information updated from time to time, e.g., anything even vaguely blog-shaped, make sure that it has RSS and Atom available so users can monitor it any way they want. Don't waste time building blog hosting or blog aggregating sites, since they are already widely available and an African one would be just like an American or European one except perhaps for translating the messages into local languages which they can already do. Maybe you can get Google to put a blogger.com site in Africa to speed up access for African users.