I tried rotating a view on a layout once and the PDF file blew out too. I traced the problem to a fill pattern that, when the view was rotated, seemed thik it was a lot more complex than the non-rotated version.
On another (similar) note, we have discovered recently that text rotated for an alternative master title block does not justify or format correctly, when published to PDF. The original text was "spaced" and rotated 90degrees, which looked fine on the master, but went to normal (100%) width in the PDF. When right justified, this produced an incorrect result.