I really don't like the way that WordPress names thumbnail/medium images based on their size.
In the media settings, I set the size of the images to fit my template design. During a recent redesign, I needed to change the dimensions of all thumbnail/medium images so I used a plugin to rebuild them. The problem is that since many of the images were hardcoded into posts, after rebuilding the thumbnails, I got a lot of broken links.
Unless there's a plugin that could do this, I would really like to see two things in later versions of WordPress.
1. An option in the media settings to set how generated images should be named.
2. An option to rebuild the generated images based on the thumbnail/medium settings.
Thanks to the whole WordPress community for the great work!