I agree with your comment here! I really do like the complexity that both works don't shy away from - "in addition to being a nerd and a charmer he's also a drama queen, a workaholic, and an arrogant whiner with anger issues who cheats on his wife and exercises staggeringly bad judgment on a regular basis", hee, exactly!

I don't agree that the lines are clearly drawn as Hamilton=liberal and Jefferson=conservative in either Chernow's book (which I've just finished) or the musical. It's a lot more nuanced than that, even in the musical - yes, Jefferson's poking fun at "too many damn pages" echos modern politics, but so does everything in The Election of 1800 - I think LMM is not so much drawing lines as pointing out that the machinery of politics hasn't changed much in 200 years.