Last week Scott Guthrie (ScottGu) provided a first look at the new .Net Web Technology Roadmap. It gives a great overview of the improvements and enhancements in ASP.net, Silverlight and IIS 7.0.
My colleague, Harry Mower, posted an interesting blog post that highlights the roadmap for Windows Media. Specifically, he highlights the IIS7 Media Pack and Windows Media Services 2008.
Sean Alexander also posts a follow-up on Media and Silverlight 2.0 that points out Silverlight Streaming by Windows Live and highlights Expression Encoder and Silverlight playback capabilities.
The web is about more than AJAX, the next web will facilitate broadcast of media directly to the consumer in new ways. Given this expanded view, it's hard to put together a "roadmap" that suits everyone. The bottom line is that Silverlight delivers a great user experience, and both Windows Server 2008 or Windows Live provide a great content delivery option.