I'm willing to root my Android. I've just been frustrated having to manage the process of updating my phone anytime a new OS comes out (as opposed to having the carriers do it), and the experience I detailed with doing something as simple as clearing the data from my iPhone makes we wary of doing this. Fortunately the Android community is getting better and better and producing root tools that you can simply download as an .apk, which is what I did with my Droid. This process does not work for my Galaxy, so I will probably end up manually doing this. I am worried that I will brick my phone since it is unsupported.

Hopefully the takeaway from this post was not a debate around root or jailbreaking, it was that there is a fundamental difference in the market forces playing out here. I always find that personally interesting, and personally frustrating right now.