I make my living in the Java based web world and I would not recommend it because it is not nearly so programmer productive as other frameworks like Django. I

I make my living in the Java based web world and I would not recommend it because it is not nearly so programmer productive as other frameworks like Django. I would expect the same would also be true of C#. You really want something that you can use to get a site out quickly and revise just as quickly. If you go at it from a desktop C# point of view, you are probably going to make a number of fatal mistakes. I did some job hunting recently in CA and I came away with the feeling that the companies developing in that environment are really not doing anything interesting. think there is a mindset in that world that will hold you back. My best advice is to pick Django or Pylons or Rails and do a 2 week code sprint to implement a prototype of your idea. I think that will answer a lot of your questions.