UGH. Sorry for posting. I figured out the top circle needs to be filled using Planar in order for it to work.
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This video shows me trying to blend but with little luck: It keeps saying "Calculation Failed."
http://youtu.be/Sa7EFH-j3cs
Here's the file: https://altuit.cloud/web/dbpub/3D/blendissue.3dm
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