My first choice will be the HR, as long as I have 1-4 cat certificates. I would lever pay the regular rate there. If I run out of certificates, my second choice will be one of the brand new Marriott properties around LGA. The TWA hotel maybe OK once, for the novelty factor.

You can get the TWA for around $250 sometimes, which is still a lot, but ok for once.

For the HR the Ubers from JFK terminal 4 are very convenient. They are right outside arrivals, with a 2-3 minute wait time.