Unfortunately, the question is harder to answer when put naively. How is a beginner supposed to evaluate what somebody says about closures, lambdas, type checking?

I would recommend learning Python. Python for Windows is a very handy environment; you can fool around with Google App Engine if you care to, or run Django or whatever locally.

I would recommend rephrasing your questions along these lines: I am a beginner interested in starting with web applications. What languages and frameworks do you think most promising to learn on, and where can I find good examples to illustrate the principles?