1. Nitrous tends to give the most additional power for the least amount of money, so it wins "bang for the buck" when you're on it. Of course, you're not on it all the time, only when you decide to use it. Headers will nicely supplement any forced induction mod.
2. Rather than low end torque, I would think the bigger difference between nitrous and a supercharger is that the SC is always there and working, whereas the nitrous is only on demand. Also, even the BaschBoost, which is the least expensive supercharger, is going to be (slightly) over your stated price range.
3. No one can guarantee whether your transmission will, or won't, be fine. That's a risk that you will need to consider. Furthermore, I don't think anyone (even Mark Basch, who probably knows better than anyone in the world) can say, with confidence, that there is an x percent probability that a failure will occur. (Correct me if I'm wrong, Mark, and if so, tell us what x is.)
Weigh the cost of the mods, the benefits, the (unknown?) chances of a transmission failure, and the cost of fixing/replacing the transmission if one occurs, along with your personal tolerance for financial risk, in order to make your decision.
[This message has been edited by nsxtasy (edited 17 July 2002).]