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We have an ASP system that we are going to replace with ASP.NET. This system is used by several different entities as an extension of their website (external of this system) using virtual directories, CSS, etc. Is this architecture still sound in the .NET world? Is there a better way of doing this?
Virtual directories are a feature of IIS. CSS can be used in an ASP.NET application, and what gets sent to the client/browser is still HTML/CSS/JavaScript, no matter whether the server side is implemented in ASP or ASP.NET.
So you will probably be able to do everything in ASP.NET that you have done in ASP.
Although ASP.NET offers lots of additional features, such as VirtualPathProviders, HttpHandlers, HttpModules. These are all things that were not possible in ASP (at least not without programming C++, ISAPI stuff).
Although it’s difficult to tell what might be of use to you, since your question is a bit vague.