I really think it is up to you. I personally love the S2000 and think it is one of the most well built engines out there but my teg has sentimental value to me. I too have put tons of money, time, and care into my car, but I don't think I would give all that up for an S2000. That is just me, and the decision is really up to you.
I am being anally raped on insurance as it is, I wouldn't even begin to imagine how much it would be for me to drive an S2000.