WYSIWYG ImageField is my latest Drupal module, a module designed to help bridge the gap between WYSIWYG based inline image management and the power of The CCK based ImageField module.
It originally came about while working on a site for a client, the designer had provided guidelines on how inline images should be rendered, with multiple options, to keep a clean look to the site content. Unfortunately the standard behavior was to use the IMCE module to give the client a seamless WYSIWYG experience. The obvious negative to this practice is the lack of control and extensibility one could achieve by the use of the ImageField module.
My previous thoughts on this issue (because it is an all to common issue) was to go with a simple configuration of ImageField and the Insert module, coupled with a few ImageCache presets. While this worked fine for me, it just wasn't as simple and as integrated as IMCE for a client to wrap their head around.