The only way I found to solve the problem of text not rotating along with the
autoshape is to fool Word into believing that the shape is now a picture; you
can rotate pictures. First, on a blank page create your autoshape, insert
your text and do all the formating you need. Then copy the autoshape on the
page where it will be used but not on the picture or chart yet. Then click
Edit, Paste Special, Microsoft Picture and you've now inserted a "picture" on
the page. Grab the corner and stick it wherever you need it and you can
format size, etc. (as a whole - not individual components of the autoshape)
through the format picture menu.