I worked in right Times Square in the JVC building for about 15 years a while ago. I remember $5 packs of gum until you told the guy you worked in the building behind him and then all the sudden it was 50c.... Expect that kind of gouging. Now for New Years Eve it is unbelievably packed, everywhere from 42nd up to Radio City. And unless they changed things once you are in that area you can not get out, not even to use a bathroom. And unless you want to be a mile away, plan on getting there real early and have an empty bladder.
Unless you lost a bet or have some overwhelming desire to scratch this from a bucket list, I would avoid it like the plague, even if you won the trip for free.