I was fully on the Hamilton bandwagon back in 2015 and I just saw it for the 19th time last month. The performances are still uniformly strong, and I still got emotional and excited at the right times. To me the one thing that seems dated is the costumes. In 2015 we were firmly in the grips of skinny jeans and big giant chunky boots style era. Yes I know the aesthetic in Hamilton come from the 18th century footwear style, but 18th century women didn't walk around in giant boots and leggings. Now that mom jeans are back in style, it does look "throwback."
As a high school teacher, when it comes up with my students, they only reference it as being on Disney+, and they are confused when I talk about going to see it live, asking why anyone would do that, etc.
The tour in Chicago is promoting its low prices which is never a good sign. And....shocker of all shockers, Hamilton is up on Hottix, which is Chicago's equivalent of TKTS. We are definitely a long way away from people saying "I only had to sit on the sidewalk for four days before I got tickets!" lol