Re: Microsoft CAL licensing
The Web Server thing is really very simple. Hosting Providers have other forms of licensing agreement from Microsoft that allow them to licence the software making this a non-issue. There are also other options (and yes, it will depend on the scenario).
For example, Windows Server Web Edition exists for pure Web Hosting scenarios (at least "did" - it might be gone now and personally I don't care enough to check).
There are External Connector licenses that permit usage you describe in some scenarios.
There are of course 2 options if you're confused:
(a) Get a Microsoft Licensing Specialist to give you the correct options to stop your constant moaning.
(b) Use a product that does not require those licenses. I hear that Open Source is often a good place to start if you're more concerned with licensing than other costs which may or may not in any given scenario work our more or less cost effective than the other.
It is recommended that instead of moaning a lot you get proper advice.