This is something we always struggle with. You asked for some thoughts on how we could address the two main issues, so here’s a start on how you could allow clients to place images inline without a bloated editor. Allow a customer to upload all the images they would like to see in the content, then present these somewhere on the page as thumbnails with some kind of ID—could be as simple as “1”, “2”, and “3” if there are three images. Then some very simple reference to those in the “MarkItUp-like” editor would be enough to place the images where the user would like in the content. Just a starting thought for further discussion. You are right, this needs to be fixed. We’ve lived too long with the same old problems…

Great post, thanks for starting the conversation.