Headache rack+ hitch extender

Hey all! Has anyone used a headache rack along with a hitch extender set in upright suv position to carry long items? I occasionally need to haul a long ladder and longer lengths of lumber, plus also a 17' canoe. Cargo weights would be 200 lbs. max. I was thinking this may work for occasional use, plus I would be able to retain a tonneau cover, and not have a rack in the way all the time. Just curious if any one has done this. Did try a search but come up empty, also Google search is absolutely horrific. Thanks for any info that you all could pass along.