Vista Flickr Uploader is a small tool I found at CodePlex to quickly push a whole bunch of pictures to your Flickr account.

Pros: Allows you to select a whole bunch of images at once, allows to assign the images to a previously created set and remembers the folder you picked pictures from the last time.

Cons: Takes some time to start since it validates the verifies application requirements every time, does not allow you to create title or description of the photos and finally the code is under LGLP - no way that I touch it.

Nice, but some room for improvements.