There was a great TED talk I watched a couple of years ago where a young lady talks about traveling and expectations vs reality. The gist of it talks of when we travel somewhere we HAVE to see certain landmarks, but in reality they are far from the images we have seen thousands of times in tourists guides and the likes - often leading to disappointment.
For the life of me I can never find it but in all honesty Cyberdemon’s trip sounds a lot better and more achievable than your version. I get that you want to see landmarks, I really do and we are all guilty of that when we travel but everything on your list is so catered to tourists that you can get as much information from Googling it as you can standing next to it.
I can’t speak for the West Coast as I haven’t properly been but I did live in NY for two years and I can say Brooklyn is boring as an area, what makes it is taking your time, eating in a restaurant and mingling with the local hipster folk, I guarantee visiting it for the day you’ll be underwhelmed for sure. The same with Manhattan, once you leave the tourist traps of mid-town (if you ever do) you’ll find a different vibe if you’re in the West Village to the East Village or even if you start on the Upper East Side and wonder across the park to the UWS. My advice would be not to try and fit everything in to the trip and try make it your own.