CCC 5 can work on V3 and CCC 4 can work on V3 and CCC 5 can work i suppose....
The main difference between them is the reporting engine and the ability to run reports from MS CRM and of course in CCC 5 the vital parts ( DeltaServer and Reporter ) are services and webbased.
Do not upgrade for the upgrade, be aware that any new software incorporates new bugs wich will be fixed in later builds.
What version of IIS have you installed on the server?
I had similar problem problems when trying to upgrade a Windows NT Sever(IIS V4.0) but it was fine on windows 2k
Also, I can't positively remember which way at the moment (I think IIS second) but there is a required installation order between .NET and IIS on the CCC server. Perhaps you installed them in the wrong order? Easy to do if one of the components was already loaded when you started your CCC install.
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