Welcome to HTS. No these are really good questions and I'm learning about this myself. So good timing. But I would advise against using windows.
1. Yes you can. Read this.
2. Yes. But again with windows you are limited; Cain and Abel and I've heard of using Etheral.
3. Not sure how to do this on on windows but read over this SSL Strip
4. I'm fairly certain you can but I'm not sure off of the top of my head how to do it. Something I still need to research.
If you decide to switch over to using linux (or backtrack) you and I could talk more in detail about this lol. Also, by all means post some details of what you are learning. We could both help each other out.