1. It is possible, but only if you expose the VB
.NET DLL as a COM or COM+ object and install it into the GAC. Classic ASP is a scripting technology and it can only do late-binding to call into COM DLLS. The CLR always locates a DLL using fusion, and NOT the COM registry (although it does have to be registered for the benefit of ASP). This means it will look in the application directory and the bin subfolder, HOWEVER, you don't have an application directory because you're calling the DLL as a COM object, so it must be loaded in the GAC in order to be found. Do some web searches to learn how to deploy the DLL to the GAC (which requires giving it a strong name first).
2. This forum is for the book "ASP.NET Website Programming Prob-Design-Solution", so this question is off topic here.