Hamilton vs. Jefferson?

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Hamilton was ineligible for election to the office of the Presidency.

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While Hamilton does not meet the first possibility, he does the second as he was citizen of the United States as of 4 March 1789.

Quite. I had forgotten that.

Here's how I see the election playing out if it were held today:

327/211

This election is largely a battle between the populist Jefferson and the elitist Hamilton around many of the same issues they waged war over in their day, simply adjusted for twenty decades of development. Hamilton represents a similar sort of political alignment Rudy Giuliani did in the 2008 Republican primaries, namely financial investors hooked into the system of State subsidies and bailouts. Jefferson is able to combine populism with minarchism, excoriating Hamilton and his corrupt capitalist friends for relying on the government for economic support. The high-churcher Hamilton strikes back at Jefferson on social issues, lambasting him as a closet atheist and a radical looking to upset the established order.

The conflict turns on the Southland, with the old New Dealer bastions of Arkansas, West Virginia, North Carolina and Georgia giving Jefferson the edge he needs to outflank Hamilton. But Hamilton is able to keep it closer than might otherwise be expected because of the toxicity of Jefferson to religious conservatives. Alaska delivers to Hamilton the highest vote percentage ever recorded in that State, with the many oil businesses there mortified at the prospect of being cut off from Federal patronage.

Michigan, surprisingly, defects from the Jeffersonian camp, alarmed at the possibility of being forced to repay the bailouts of 2008 and frightened by Jefferson's anti-government rhetoric. The Atlantic coastal States also stick with the native Hamilton, buoyed by Wall Street's influence.

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I'd think Connecticut would be  shoo-in for Hamilton in the above race. What I'm wondering about is the more Liberal side of Jefferson when reading your description of a modern race. Jefferson was probably majority Minarchist, but he also called for re-distribution in order to level the playing field. That might help in the West, but among the uber-rugged individualists (not saying they'd vote Hamilton), that would still be the sin of government interference. I see Hamilton doing better in Maine, Wisconsin, and Illinois than you give him credit for. (not that I"m a big Hamilton fan. I thinkthey both had good and bad qualities)

Jefferson believed, as do I, that government intervention in the economy is almost invariably to the benefit of the wealthy elite. Odds are his platform would be a sort-of liberaltarian synthesis, which ought to allay the fears of individualists.