Because of I had run into some trouble while implementing PlexConnect here some hints and additional infomation how it works in the end. ;-))
General guide:
https://github.com/iBaa/PlexConnect/wiki/Install-Guide
Windows installation guide:
https://github.com/iBaa/PlexConnect/wiki/Install-Guide-Windows
Certificate guide:
https://github.com/iBaa/PlexConnect/wiki/Install-Guide-Windows-Certificates
Install Wifi-Guide
https://github.com/iBaa/PlexConnect/wiki/Install-Guide-AppleTV-Wifi
PlexConnect as a service
https://forums.plexapp.com/index.php/topic/88368-how-do-i-start-plexconnect-on-startup-on-windows-and-make-it-seamless/?p=512401
Needed software:
Python 2.7.x: http://www.python.org/getit/releases/2.7.6
Keep the the installation path c:\python27
OpenSSL: http://slproweb.com/download/Win32OpenSSL_Light-1_0_1e.exe
Keep the installation path direct on c:\openssl....
Optional if OpenSSL gives you a warning, that the Visual C++ 2008 Redistributables are missing:
Visual C++ 2008 Redistributables: http://www.microsoft.com/downloads/details.aspx?familyid=9B2DA534-3E03-4391-8A4D-074B9F2BC1BF
(IMPORTANT: you need the English version, otherwise OpenSSL will still gives you the mentioned warning)
If you get an error while creating the certificate, e.g. ...plexGDM...line 120... please check the following thread
https://forums.plexapp.com/index.php/topic/88639-plexconnect-error-import-plexgdmline-120/
Maybe you have to set the path variable for OpenSSL. In my case this helped
http://jaspreetchahal.org/warning-cant-open-config-file-usrlocalsslopenssl-cnf/
After that OpenSSL works fine and the certificate was created successfully.
If you get an error for port 80 please check the following thread:
https://forums.plexapp.com/index.php/topic/88912-error-10013/
Run CMD. Execute "netstat -anbo >netstat.txt
Open the txt where you have executed netstat.
Search for ":80 ". If you find an EXE you must disable or change the process/program/service, so that port 80 is free to use for PlexConnect.
If you have no specific EXE which is using port 80 it is probably the system process itself. Tricky to find it out but not impossible.
In the board you find sometimes the "Windows process activation process". Go to the Computermanagement\Services and kill this process and try it again. If port 80 can now be used set the process from automatic to manual.
If you still have problems I think you have to kill each service one by one like me in my case. In my case it was the "Web Deployment Agent Sercice" which had blocked the port 80 on my WHS2011.
Be sure that you have the correct inbound firewall rule. On my Win8.1 client the firewall rule was created automatically through accepting the firewall waring (see guide). On my WHS2011 the warning was not displayed and I had to created it manually.
Now you are ready to use PlexConnect. If you are sure that Plex and PlexConnect are running you can set up PlexConnect as a service. Follow the above mentioned guide.
Hope this topic is helpful for one you runs also in trouble like me.
AND: RTFM!!!!! ;-))
Alex