Barack Obama's candidacy was one of the most web-enabled we've seen and it looks like his transition and presidency will be as well. The transition, for example, will be on line at change.gov.
There are several cool spots on flickr that are focused on our president-to-be. There's a group called "A message for Obama" that invites users to post photographed messages for the President-Elect. I made mine with wordle.
There's also a fascinating set of photos from back-stage with the Obamas, the Bidens, and friends on election night. This photo of Joe Biden greeting Sasha Obama is my favorite.
I think this web-connectedness is part of why I'm so excited about Obama. It's not just that he's using the web the way it can and should be used. It's also the fact that it doesn't seem at all forced; his techie-ness is natural.