I can't believe it but I actually got Hamilton tix - face value through an Amex pre-sale!! My 22 yo daughter and I will be there for 2 nights in mid-May and looking for suggestions on your fave neighborhoods. Our show is a Wed matinee, so we'll have 2 free nights and another completely free day. I lived outside the city as a kid and we've both been multiple times as adults, we'll skip most of the typical "touristy" stuff. We may go to another show or see the taping of the Daily Show or John Oliver if we can. Keeping the agenda open but looking for some cool restaurants, great walks, museums etc. Where do you love to stay? And I know it's going to pricey but any "hidden gem" lodging that's a relative bargain? Thanks!

For NYC hotels, I've often gotten good deals on:
http://www.travelzoo.com

It's too early for next May, but you can sign up for notifications of offers.

Note that many colleges and universities schedule commencement in May. (Columbia University's is May 17.) You may want to secure reservations at an acceptable hotel that you could cancel later as you continue to search.

We, too, use travelzoo for NYC hotels. Relative bargains are sometimes available through a hotel's membership program. Most hotels offer special rates for seniors and AAA.

Without knowing your budget it's very difficult to make recos - except to be prepared for very high rates that time of year.

I have yet to see Hamilton and I can't imagine seeing both of these in the same weekend but I just returned from seeing Come From Away in DC and the Amex Pre-Sale for tickets starting in Feb is Oct 11th. If you wait for reviews on Didhelikeit you can schedule a different trip in a few years.

http://comefromaway.com