I'm currently running a small website on wordpress. It's main focus is just to deliver newsarticles covering a small geographic area (a town...).
My main problem is image handling and making it as easy as it can possibly get. Most of my contributers are old and not to good with computers. I find wordpress ok, but inserting images in the TinyMCE editor and fine tuning by moving them around the paragraphs is not an easy task and its been quite a hassle for basically everyone beside myself.
Here's an example of a solution that I've been thinking about. (Norwegian site... sorry...)
http://innsida.no/article/20090328/KVINNHERAD/4896471/1019
The important concept here are the small images which is in the column to the right. I'm thinking of an CMS solution where the user just uploads the images into forms, and then the CMS + CSS styling takes care of the rest.
So the user would just input:
1. Header
2. Teaser / Lead in
3. Story
4. Main image with image text (just click a browse button and find the image on the harddrive, the CMS scales and reduces the jpeg quality to get a nice small file.)
5. Additional images with image text (just click a browse button and find the image on the harddrive, the CMS scales and reduces the jpeg quality to get a nice small file.)