Say No To This - Hamilton Should've Taken a Break

Hamilton should've taken that break he was offered a bunch of times.

In Say No To This, Hamilton states that he needed a break. The song before this was Take a Break, in which both Eliza and Angelica offered him a trip to upstate New York to stay with Philip Schuyler (their father). They both told him to "take a break" multiple times, all but one of them referring to the trip (the only one that was not referring to the trip was when Eliza told Hamilton to take a break to listen to Philip Hamilton's poem).

However, in Say No To This, Hamilton states that "I hadn't slept in a week. I was weak, I was awake. You'd never seen a b*stard orphan more in need of a break."

Now, you can claim that he needed the break since he had overworked himself due to the fact that Eliza hadn't been around to relieve his stress, but that doesn't change the fact that he screwed up his entire life because he didn't go on vacation with his family. While he stayed in New York City, he "longed for Angelica" and "missed his wife". Maybe he should have gone upstate to at least visit, if not stay for the duration of the trip.