lol, under 200/night?
1. One place you can try is Hotel Bently on the UES.
2. See Phantom, Monte Python, and Wicked. Might want to see a show at Lincoln Center, New York Phil is awesome. Rockettes might be playing now, not sure.
3. Try Rare/View, Sparks. Get a Carls Cheesesteak in Murray Hill. Grab a brew at McSorleys. Get a pie at John's Pizza or a nice Italian meal at Carmines if you're grabbing a show. Galway Hooker is fun, as are any random "o-bar" in Manhattan (O'Hurley, O'Brien...etc). Try to go to Irish Rogue, house of brews is fun too.
I am not a "trendy" clubber.
4. Statue of Liberty/Ellis, Top of the Rock (screw Empire State, bars = suck). See the tree while you're at TotR. Go to the J.P. Morgan library in Murray Hill. Go downtown, see the WTC, then rub the bull's balls by Bowling Green. Loop back up and see the NYSE and Federal Hall (George Washinton's inauguration site).