MSDN contain mountains of webcast on everything, the educational value is huge. I wish more webcast existed for Java, Groovy, Javascript, Perl, Grails, Catalyst, Spring framework!

The soup to nuts series covers everything, similarly other webcast series, the idea is simple and very effective, you will spend your first 10 or so hours looking as vidoes and presentations, next you can move to books and online forums and blogs

After he finishes these webcast, moving to RoR will be a much simpler road, even when RoR is a different framework

If you think in terms of map, fold, and filter, you'll be right at home in C#/VB.NET (they're just called Select/Aggregate/Where instead to be familiar to people whose background is SQL and not functional programming). Java, on the other hand, is agonizing to me.

You might not like it but ASP.NET is a popular and extremely effective environment for building interactive web applications. I personally use a variety of different tools to build web apps and .NET ranks with them.