There is an interesting article over at Wired magazine's website by Evan Ratliff, entitled "The Wired Presidency: Can Obama Really Reboot the White House?".

The various obstacles that Obama will have to deal with are discussed, including license agreements, purchasing rules, a ban on endorsements, and restrictions on revisions, among others. They even mention the Change.gov's CC license (which appeared after FGI and others wrote many many emails about why they had a copyrighted site initially!):

The Obama team was able to sidestep these kinds of troublesome rules on Change.gov, in part because, as a quasi-governmental site, it's not subject to executive-branch restrictions. They were able to post videos on YouTube, link to outside sites, and even publish content under a Creative Commons license, allowing it to be freely shared.

Here are some other good quotes from the article:

...turning his innovative campaign and transition into Government 2.0 won't be easy. The nimble Obama startup is about to be absorbed into a stodgy, technologically backward behemoth: the federal government...Ahead are bureaucratic obstacles the campaign never imagined, along with the political land mines that transparency brings.

"We know that there are a lot of people advocating for more open government," Godwin says. "We're saying, absolutely, put the data out there. But I think we have to be realistic."