I think we need to win the argument on your 1). I suspect that the Republicans will try to use the argument that doing this moves the control down to more local level. Their argument would be that it is unfair to give ALL (say) VA's votes to someone who won (say) 55%. If not countered, this could resonate - I think the Democrats would be wise to argue for election by popular vote. That kind of takes their (spurious) argument and says - we think the person wanted by the most voters should win. (Note that the Republicans did not care that Gore won the popular vote in addition to likely really winning the EC vote.)
I do think there would be a major uproar if a candidate won the popular vote by as much as Obama did and then lost due to games like this.
One problem is that the Constitution gives to the states the responsibility to choose the electors. This is a case where our Constitution's age shows itself. The founders really were not proposing a real democracy.
As to 2), obviously different candidates - or just different years, will lead to different results. I would be careful of arguing that just because a candidate did better in a state in the primary, that they have a significantly better chance of winning it in the general. (I do agree you can easily make the case they won't do worse.) I think what we need to do is fight this technique rather than hope that we can have a candidate that appeals to the Republican base. It would be unfair to HRC to expect that she could do that.
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