A few of my friends were lucky/smart enough to join up in 2003/2004 and I've been going with them about once a month or so since then. First off Citysearch needs to get their facts straight, since last I was told membership is around $2,000/year - and if you flinch at that number, don't even bother trying to get in. Members also need to be referred by 2 existing members, and go before the 'board' (or something like that) before approval. Last I heard the waiting list for membership is around 1500-2000 names long. Good luck. During the spring/summer when its nice enough for bathing-suit weather, the roof has some of the best eye candy in manhattan - think adrianna lima sort of talent - and if you're into that sort of thing, its frequented by celebrities (jay-z and lebron james were having dinner on the roof last I was there). Just understand that if you do get in here, and you do see someone famous/notable, its a absolute no-no to get all excited about it, and approaching them is a serious serious faux pas (although if you happen to be standing next to someone waiting for a drink at the bar I suppose you could just strike up a conversation with them like you would a normal person, but again good luck and do so at your own peril).
Pros: Uh, theres a pool on the roof with hot girls everywhere
Cons: Impossible to get a membership unless your on the rich register/cover of people mag