1. We are not in any way assuming that. We're saying that, to the extent that the Democrats don't "deliver sweeping reforms," fear of an activist Supreme Court overturning the legislation is not a significant factor in most cases. The Supreme Court is one of the most powerful veto points because . . . it so often exercises its veto. Not because legislation is "chilled."
2. Your argument would really be strengthened with, you know, evidence. Or even examples. So far, you provided two examples, both of which were inapt and/or inaccurate. Then I provided you with one good example, but it's also a special case. If your argument was that **sometimes** the fear of Supreme Court review can influence legislation, then the wealth tax would be good enough for at least a draw if not a win. But you've gone way further.
3. It is true that future court actions can influence the fine structure of legislation -- i.e. choosing between different mechanisms toward the goal. For instance, back to the wealth tax: I prefer a realization rule than a wealth tax per se. There are several reasons for that, one of which is that the Supreme Court will be less likely to fuck with it (though the reality is that the Supreme Court will probably strike both down).
And so too with other questions. I would not imagine that future iterations of Obamacare would rely on an insurance mandate, because though the Supreme Court hasn't exactly struck that down, the writing is clearly on the wall. So we'd take the Supreme Court's challenge: if you don't want us working through the private sector, fine we will federalize the whole thing -- the whole thing, here, being the way of guaranteeing universal care.
If this is your point, then it's solid. But I don't think this has been your point.