Best bet

check the prices at hotwire to get an idea how much it is going to cost and start bid 30% lower and increase slowly. If you arrange you bid (after failed bid, add an expensive neighborhood and increase you bit by a few $) carefully you can bid several times at once after which you may have to wait a few days since they won't let you slowly inrease you bid. You have plenty of time. Ocasionally you get a steal. Never did NYC before, but my first time bidding for Hawaii was great. Hotels (4* on Wakiki) cost $300 direct from their website can be had for ~$120.