Might I suggest tumblr.com for a Flat Stanley (Flat Emily?) travel "blog"? We could start a page that would get the web address [ourpage].tumblr.com, and it's essentially a very simplified blog format that would be very easy to use even for people who have never blogged before. We could share the username and password along with Flat Stanley (write it on his/her back?) so whoever has it can upload a picture or video and a little blurb about where the picture was taken. We wouldn't need a central webmaster that way, and everyone could track Flat Stanley's progress as he/she traveled
ETA: steps to post something to tumblr:
1) Go to the site
2) Log in
3) Click the giant "photo" button at the top of the page
4) Upload the photo (plus text, if you want)
5) Voila, it's on the blog!