As an update in case anyone is curious. No one ever called me back from AMEX, so I called them back yesterday to ask about this. Apparently they had opened a case to figure out why this happened, but no one actually decided to look into it, so there were no notes, and nothing had been done.

I spoke with a supervisor and he told me the reason that the miles didn't transfer is that the AMEX servers had an issue connecting with ANA (i.e. not anything to do with personal info mismatch or anything like that, 100% AMEX's fault). I asked him why no one would contact me and why they wouldn't fix this by contacting ANA and figuring it out so that I could get my miles, he had no response.

His final resolution:

They reimbursed me the $475 I spent on miles AND they took away the 19,000 miles they had transferred to my account (basically just rolled back my miles purchase)

To be clear, I told him I didn't really care much what path they took, that I just wanted them to have better customer service and actually help me when things like this happened (and I wanted to be able to use my miles when I need to!). Bottom line is, I lost out on 2 flights I was trying to book, ended up giving them money, and got this money back, so for 1 month and a bunch of different phone calls (few hrs total) I end up exactly where I was a month ago, seems like terrible customer service, and I told the supervisor that while I appreciate his gesture, I thought the overall interaction was really bad.

Compare this to when I went to a michelin starred restaurant a while back and got sick. I wrote the restaurant just to let them know that my wife and I got sick, admitted it probably wasn't their fault (no way for me to know if it was just a random thing), but that since they source local that they might want to look into it and keep an eye out for other customers that night. They called me back and reimbursed my entire meal (I forced them to keep the tip) over $500.