Many of our best developers didn't know C# or ASP.Net when they started. That doesn't appear to be a huge problem if you find the right person.

We've actually received quite a bit of support from Microsoft (free software, design review sessions, books, etc).

http://microsoftstartupzone.com/blogs/ebt_success_stories/ar...

As for cost effective licensing: http://www.microsoft.com/serviceproviders/licensing/default....