Listen up! (Score 1)

Alright, I don't have a lot of time here but this information should (hopefully) answer some of your questions and set the original poster straight.

1. This has nothing to do with the OLPC Project submitting to the terms of the Fedora Project Individual Contributor License Agreement. It also has NOTHING to do with the GPL. These don't matter, period. The OLPC project is run by Americans, in Cambridge from what I gather. This means that the OLPC project was already subject to US export regulations, regardless of any license agreement or what have you.
2. Yes, the hardware is also subject to US export regulations
3. The Fedora Project Wiki entry for Legal/Export is outdated and inaccurate. For example, Iraq is still listed under "Embargoed Destinations". Iraq is not embargoed (*somehow* that changed when we invaded)
4. There are two US agencies that are important when discussing the Cuba sanctions/embargo. The Department of Commerce and the Treasury Department.
   • Here's a nice 6 page overview of the US embargo of Cuba from the Office of Foreign Assets Control (Treasury). Notice the text stating:
     To whom do these sanctions regulations apply?All U.S. citizens and permanent residents wherever they are located, all people and organizations physically in the United States, and all branches and subsidiaries of U.S. organizations throughout the world
   • And here's a nice overview from the Bureau of Industry and Security (Commerce) discussing exports and reexports to Cuba. Note that you will need to obtain a license from BIS for shipping something like an Xbox or OLPC to Cuba. Also note that there is a general policy of denial in place (meaning it's unlikely that these exports will be authorized by BIS)
5. No, you can't be a "middle man" or you'd be violating US export control regulations. There are these pesky things called General Prohibitions that, you know, "prohibit" certain things. General Prohibition 10 in Part 736 of the Export Administration Regulations states:
   You may not sell, transfer, export, reexport, finance, order, buy, remove, conceal, store, use, loan, dispose of, transfer, transport, forward, or otherwise service, in whole or in part, any item subject to the EAR and exported or to be exported with knowledge that a violation of the Export Administration Regulations, the Export Administration Act or any order, license, License Exception, or other authorization issued thereunder has occurred, is about to occur, or is intended to occur in connection with the item

The US export regulations are the broadest in the world, with more unilateral controls than other other country. I could write a friggin book here, but I'll stop before I ramble any further. Let's just sum it up by saying that this article really isn't news at all and nothing has changed for the OLPC project (in regards to export controls). Microsoft can't ship Windows or an Xbox to Cuba, and the OLPC project won't be selling laptops to the Cuban government unless they get a license for it.