Neilo,
That sounds identical to what my situation was like with IIS. In fact, I remember finally asking the server company why I paid nearly 300/month for what was the worst experience I have ever had in computers. They would always act like the cryptic nature of it was just part of the deal. I spent many hours on the remote desktop trying to set up sites and make sure I had all the necessary programs and services running. I never could get it to run smooth. So, that's what ultimately forced my hand in switching from expensive ColdFusion IIS-based hosting to PHP on Linux and everything has been far better. In fact, I think I became a better programmer overall when I started over and learned PHP from the ground up.
Regards,
Brian