Moxie did provide a more detailed attack description. I had to correct an iptables command and modify sslstrip to alter the JS but otherwise his instructions were complete and correct. Per the original instructions, he should have had to configure the proxy but that's purely a function of who does that labor so I happily did the small amount of extra work.
Once I completed the attack, I learned as I suspected from reading about sslstrip, the SSL certificate was removed. I thanked Moxie for his efforts and praised his work but informed him that it didn't meet the initial requirements. He argued that it works in the wild and that I could acquire appspot.cc and a certificate for that. I replied that if he wanted to conduct a convincing enough demo that I would be fooled into clicking, I'd consider that sufficiently close to being valid. Alternatively, he could produce an SSL certificat e that the browser would accept as valid for that domain. I agreed that a user in the wild might not be as cautious but that in agreeing to route my traffic through a malicious proxy, I recognized I was giving an attacker a significant advantage and that's why I made a valid SSL certificate a requirement in the initial post.
He replied back that any LAN can be malicious so he disagrees with my assessment and that he didn't trust I wouldn't throw up more unreasonable objections and that I should pay.
I replied outlining exactly how I would evaluate any alterations to the MITM he's proposing. It was at this time he posted to twitter. I heard about that and emailed him and he denied he was accusing of of dishonesty but only noting that I had declined to pay the reward tptacek thought he was owed. I remained concerned that it wouldn't be taken that way and unfortunately tptacek has proven my fears correct.
In any event, I asked him if he believed his approach genuinely met the valid certificate requirement at this point because I wanted to assess whether he was he felt my rules were unfair or that I wasn't abiding by them. He declined to reply to that question.