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When I'm editing a page with an attached style sheet, and I drag the handles on an item in the Design pane, the style element is added to that item's HTML tag and not changed in the attached style sheet.
It takes quite a bit of time to cut and paste the css values from the HTML page to the style sheet, I just can't imagine that this is how it's supposed to work.
I could not really follow you unfortunately on the layout you provided, but hopefully the page editor options will help