Did you generate and install the SSL certs to the PlexConnect folder and the ATV?
yes I created the ssl certs, I moved 2 of them to the cert folder in the plex master folder then,
I used the iphone configuration utility to install the cert onto the atv, after selecting install, it did change to remove which is the only confirmation that it should have worked, BUT, the instructions state if that worked you shouldn't have to create a 2nd profile on the ATV, in my case, I did have to do that.
So I went to the ATV and created the 2nd profile by entering the http: my ip address above/trailer.cer (typing this from memory can't remember if I typed trailer or trailers) but none the less I followed those directions.
You should have only one trailers related profile on the aTV. Either via iphone configuration utility or directly using PlexConnect WebServer.
Did you set your DNS Address on aTV to your PlexConnect host? I am missing DNS related lines in your log.
After installing the cert via usb and the iphone utility it did NOT create a trailers profile on the ATV2 which is why I manually created one. My IP address is the same for everything, my Plex server, my computer, my DNS setting on the ATV2 are all the same IP address which is what I got by following the directions, let me know if that's wrong.
Did you set inbound rules for TCP and UDP for Python.exe?
NO, I did nothing with python.exe ecxept to click it, which is all the instructions said to do, I do not know how to set inbound rules for tcp and udp.....this process is unfortunately a little over my head but if you would be willing to explain what you're saying I'll most likely be able to pick it up