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You sound like you're at the same place as I was when I was your age. I was accepted into my top choice college, so I'm confident in the advice that I'm going to shell out.
Scholarships: Check out Fastweb (http://www.fastweb.com/). Once you join the website, you have access to hundreds of thousands of scholarships that are available to you. Apply to as many as you can, because even if the award is only $100, that's an entire textbook that you can purchase.
Money: Like I said, scholarships are great. Also when you're applying to schools, see if they offer any scholarships related to your fields of interests (ie. Engineering, Theatre, etc.).
Transition: If possible, try some over-nighters. I lived overseas so was unable to schedule any, but they would definitely give you a feel for the environment. There's a book I read during the summer after senior year, called "1001 Things every College Student Needs to know" by Harry H. Harrison Jr. It gives you some information that can be useful.
Academics: I took the SAT in June of my junior year, and then took it for a second time in October of senior year. I never took any SATII tests or the ACT, but I know some schools really recommend or even require those. So definitely check. Collegeboard.com has a college search which includes all that information.
Other: Even though you say you're very involved, make sure you have a focus. Schools like to see students who have a specific passion. For example, I played 3 sports, was involved in the NHS and Key Club, etc. But I made sure I emphasized my passion for traveling. This shows the school that you're not just some robotic creature who wants to attend a tier-1 school, but that you're a person who is committed and passionate, and will be a positive member of their community.
I hope this gives you a pretty good idea of the preparation. If you have any other questions feel free to ask me. I'm the oldest child of my family so I didn't really have someone to guide me along -- so I have a pretty good idea as to how daunting this process can be.
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