To re-arrange the Callouts on the left:
1. Click on the Callout pagelet.
2. Open the Inspector.
3. Click on the Position arrowhead to move up or down:

Note: Callout Pagelets are *NOT* included from the parent page. They have to be recreated on the child page.
They are keep on duplicated pages but the rearranged order changes. This seems to be affected by which side the Sidebar is.