I usually come in via Grand Central Terminal, where there are lots of machines. You can use the same card and swipe it multiple times for multiple people. The machines will let you recharge the card. The card is good for about a year, I think. If you do a $20 card you get "bonus" free rides on the card.
The major terminals (e.g. Port Authority, Airports, Train Stations, many subway stations all have machines. Easiest is probably finding a subway station.
Good luck & have fun.
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