WordPress and the Media Manager
WordPress has an impressive built-in Media Manager to help manage photos and screenshots used in posts. It includes a slick multi-file upload tool, drag-and-drop support, basic photo editing, automatic image resizing, simplistic galleries, and it provdes full control over how images are positioned in posts.
Despite all that, I rarely use it, and actively avoid using it as much as possible. I know, I just said it's wonderful. So why don't I use it? And why might you want to consider abandoning it as well? (Note that this will be much easier to do if your site is just starting out, as opposed to being well established with hundreds of images in the Media Manager.)
While the Media Manager has a number of minor interface issues (in particular, browsing large collections of images is a real pain) that make using it harder than it should be, there are two main issues that drove me away from it: poor organizaiton and a lack of portability.