Is it better to let states change their electoral allocation individually than to pursue a Constitutional amendment that would be hard to pass?
No. If this were the case, each state could make its own, and not necessarily timely, decision about the issue and some awful things could happen. Say, for example, that despite no amendment to the Constitution, California decided to switch to proportional allocation (like Colorado is planning to do in 2004), but Texas decided to keep its traditional method of winner-take-all allocation. Although the outcome of elections in California would distribute its electoral votes more properly, Texas would still be awarding is massive number of votes in a winner-take-all style. The only way for this plan to work, that is, for states to change their allocation on their own without an amendment, is for them all to do so in a uniform manner at the same time, which is even less likely than a federal amendment.