As a result of my recent transition away from SquareSpace, most of the image links from the blog were broken or redirected to the SquareSpace image attachment server. I tried using a few WordPress plugins to grab the images and store them, but unfortunately I had to go through every post one-by-one in order to get everything properly hooked up.
For those of you running into similar issues, I recommend this WordPress forum thread. Moe Loubani, one of the posters, managed to modify the popular image export plugin for WordPress in order to work slightly better with SquareSpace hosted images.
One upside: I was able to update all the out-of-date Macromedia Flash-based YouTube embeds. I wasn’t able to find the original source videos for some of the content, but at least none of the posts are littered in dead images and links anymore!