I find that almost all CMS's have horrible image-handling routines.
Most are based on an image library, while in my experience 90% of all images used for illustrations in articles are never re-used. The libraries just become needless extra steps to go through.
Also, most solutions only work with single images. If you want to insert 10 images in an article, you will have to perform the same procedure 10 times.
Does anybody know of solutions that allow me to select multiple images from my local machine, and lets me insert them into the article in one move? Preferably via drag-n-drop on HTML5-capable browsers, but I don't mind a "file open" dialog if it is only once for all images. Also I don't mind all images being inserted in one place in the article, because in most editors it's easy to drag the image to the right place.
I really don't understand why no systems make this easier, I think I could teach my colleagues how to build a complete website in plain HTML, in the time they spend fighting with the CMS...