You can watch PDFWebViewer.NET from TallComponents. This is an ASP.NET Ajax viewer that uses the PDF-to-image approach. The website has a demo version and a free downloadable trial version.
For comments, you can add some code to handle comments. TallComponents also has other components that allow you to manipulate PDF documents to add PDF comments (Acrobat compatible).
Regarding your question about Silverlight and ASP.NET, I think this is a choice that you should make based on your target audience. If you expect a large number of Windows users, Silverlight will be fine. If you need to support non-Windows users and mobile devices, you will probably be better off with html and a script (next year or so anyway).
As for your concerns about massive images for the PDF-to-image approach; that it all depends. A page image with a screen resolution will compress very well for most documents, and good PDF rendering will be optimized for the required zoom ratio. In addition, the PDF format allows you to quickly get random access, so that the rendering pages selectively look normal. PDFWebViewer.NET is fast enough to display most documents per page on demand when viewing a document.
Full disclosure: I work for TallComponents on PDFWebViewer.NET.
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