I found accommodation in Boston ridiculously expensive when I was there last year. I ended up staying in a room the size of a shoe box for about $300 a night.
I went from Boston to NY on the train. I enjoyed it and it’s easily doable. One of the best views I’ve ever seen was coming into NYC on...
When I went through in August all the auto machines were closed. They had been working in the past.
The major issue is all the flights that arrive from Australia arrive within a short space of time in the morning clogging the system up.
If you are flying with the same airline you should be fine. You will get an express customs pass to help you get through. I got through and collected baggage and rechecked with the express pass really quickly.
I haven't done clubs over there but have been to many bars and the pricing is fine.
Most bars have happy hours so that helps. Sometimes you stumble on some amazing prices. I wandered into a bar in Chicago and it was $1 beers for 2 hours.