we're running Drupal on
team2996.com (despite the posts asking about Joomla. go figure). It wasn't too hard to get set up initially, but the hardest part is getting everything looking the way you want. as with any CMS, you can either use and customize someone else's template or make your own, but granted that's harder. also, as you add extensions to it the site becomes more difficult to run overall, just because you have so much stuff going on, and some of them can be pretty intensive in setting up and getting them working.
as far as Drupal goes, I personally love the way it handles various content types, being able to set them up to display differently and whatnot, since I can have say a page with information about the team and then stories about what we're doing and have them display within the front page. it all works pretty nicely