Thanks for the reply Brummy. I ended up finding a solution.
To answer your question I was using a fresh Win 8.1 factory install. I tried it with update and without. Neither worked. I didn't load AV, or anything other than win update.
Solution: (partial) I eventually succeeded upgrading to Win 10 by using a bootable USB. I deleted all partitions on the disk. I was concerned that it wouldn't pick up the product key, but it did.