Code Shoveler opened a support ticket and after some investigation we were able to determine the cause for the issue.
In essence the issue was caused by a corrupted Visual Studio integrated help system, preventing the installer us from deploying our offline documentation.
The issue was resolved by performing the following steps:
1) Open C:\Program Files\Microsoft Help Viewer\v1.0\HelpLibManager.exe.config
2) Set the FirstTimeRun value to True
3) Open the "Help Library Manager" (in Visual Studio 2010, Help
-> Manage Help Settings
4) Select Choose online or local help
5) Select I want to use local help
6) Try viewing the VS 2010 Help (Help -> View Help)
the Telerik team