Wow, I finally got JD upstairs but that was truly miserable. However, it is doable solo.
In case anyone else is stuck in the same position here is what I did:
1.) I put JD on the landing using a dolly and leaned it onto the stairs
2.) I cut two 2x4's about 4 inches longer than the width of the nearest door opening upstairs and screwed them together
3.) Using a 30' strapped come-a-long, I used the 2x4's braced against the door frame as the top anchor and wrapped the other end around the machine.
4.) Now I slowly ratcheted the machine up the stairs, adjusting as needed to keep it on the right path.
5.) Once at the top it just took a little brute force to get it safely over the edge (I ran out of come-a-long) and a car jack with a piece of 2x12 to jack it up to put the legs on and slide it into place next to POTO...
Now I think I'm going to go take some Aleve...