did you call rewind posts?
I’ve done something similar on a site and used css to solve. The site uses 960 grid (960.gs), which comes packaged with “push” and “pull” classes that let you rearrange content relative to its position in the markup. In our case, the sidebar content is coming from a sidebar template and is called after the main content. We use the css classes to push the main section to the right alignment and pull the sidebar to the left alignment.