Hi, Matt here and looking to help you (23 years an IT developer and webmaster, former System Engineer in the bank).
Do you still need to have this done? I've checked all your references so have few questions:
1. Do you use an updated version of the ProxiHTTPSProxy ( ProxHTTPSProxyMII)? It's linked on the forum page you have provided.
2. Do you understand the whole concept? From the graph (ProxyHTTPSProxyMII) I see that you can have all set up on one machine e.g. Windows computer. So a web browser is configured to use the proxy, that is configured to pass the request via Proxomitron and the latter is configured to pass it to the ProxyHTTPSProxyMII instance again.
The configuration rules appear similar to many Internet software like Apache, squid and other. Of course my work would be to configure all on my end then pass you all the information, including with configuration(s) and helping you set up the same.
3. What computer (Windows version) do you have?
Looking forward to your reply,
Matt
UPDATE:
P.S. Please provide me any links for the software you want to use so we are using the same versions. You do not have to accept the bid yet (you have 4 weeks to do so) and I would like to proceed with tests after you message me back if interested.