I've been playing with the Flickr API. The ruby wrapper needed a lot of work and I've only begun tweaking it, but here's the start for anyone who's interested. It allows you to insert an image tag for an image from either a specific photoset or from a search of your own images. It uses simple popup dialogs and if you have a ton of images in a result set (100+), might be a little awkward. Each command lets you choose from the available sizes for each image.
You need to run the authorize command first, which will open a browser window to authorize the bundle. Then return to TextMate and confirm the dialog and it will write a token to the bundle directory. As I'm writing this, I'm realizing I should probably put that somewhere else, but it works for now.
I'm thinking about eventually making an image browser, but it would be slow so I need to think about caching the files, and at that point... I have to figure out if it's worth the time. The goal is to make it simple to insert Flickr images in your blog posts, so we'll see where it goes.