Since the entire debacle broke loose about SSL being broken in Mavericks and iOS it has been a curious few days. Now, the problem has at last been fixed. The OS X Mavericks 10.9.2 Update (Combo) patch ...
The technology is there for companies to inspect SSL traffic, but performance, management and privacy concerns combine to hinder its adoption The technology is there for companies to inspect the SSL ...
I don't find what you're saying very clear, but you do know that in IIS 5, you can only have one SSL'ed site per IP address, right? (IIS 6 on 2003 SP1 you can get around this limitation).