In 1800, when some states actually divvied up their electoral votes like this, Thomas Jefferson wrote to James Monroe with his thoughts about the relative fairness of vote-split plans:
All agree that an election by districts would be best, if it could be general, but while ten States choose either by their legislatures or by a general ticket, it is folly and worse than folly for the other six not to do it. In these ten States the minority is certainly unrepresented, and their majorities not only have the weight of their whole State in their scale, but have the benefit of so much of our minorities as can succeed at a district election. This is, in fact, ensuring to our minorities the appointment of the government.
Jefferson didn't hate the idea of assigning electoral votes by district. "To state it in another form," he wrote, "it is merely a question whether we will divide the United States into sixteen or one hundred and thirty-seven districts. The latter being more chequered, and representing the people in smaller sections, would be more likely to be an exact representation of their diversified sentiments." The problem: If every state didn't divide its votes this way, the system would be a mess, random and unfair. "Representation of a part by great, and part by small sections, would give a result very different from what would be the sentiment of the whole people of the United States, were they assembled together."