I have not studied the details of your setup, but I will just pass my general advice in such situations:
Paper and pencil!
Draw a flow diagram of your setup, and there is a fair chance, that you solve your problem quickly. When the problem is solved, make an even nicer version of the diagram which you keep. This is your personal "setup manual", that you should always remember to update when you make changes.
So when in a year when you get a new computer and everything is re-done, it will be a walk in the park to setup your gear.