My wife and I have been doing this for 20yrs two or three times a year. We take the NJ transit train in to Penn Station and buy one Metro Card and load it with cash for our estimated trips (you can always add more later). You can pass it back to the second person as you go through the style. You can't pass a weekend or 24hr pass back it will not take the second swipe so you need one for each person which may be more expensive and they will both expire on the 24th hour. Metro Cards are good till 12/31 of the year you buy them. Only take your best pair of walking shoes no matter what they look like and you'll be thankful that you did. (You can't see your feet in the Theater or Opera). We only walk or subway to anywhere in Manhattan, Bronx, Queens, or Brooklyn. Never have used Lyft and I think 1 taxi in 15yrs to get a group of us to dinner in time for our reservation. Buy a fold-able Subway map in Penn Station and you'll be fine Walk and enjoy. Check out the Highline Park. Union Square is a great transfer point as is 42st. As long as you stay under there is no additional fare to transfer. Cards work on the buses also but they are slow because of traffic but good sometimes for crosstown East to West etc. To cut down on luggage we only take one or one and a half change of clothes and just take extra underwear for the days we'll be there in two small backpacks. With the exception of your hotel desk your never going to see the same person twice while your there and I doubt very much if he is thinking "Oh gee you had the same pants on yesterday". Anyway that's my two cents worth of advice.

We're just going for the weekend. And we generally pack real light. And we're from Detroit where it's alway casual dress, even in pretty nice restaurants. So extra sox and underwear and a couple shirts, and we're good to go.