I hear ya. I have the money to spend and I'm not a tight wad. That's not the problem. If I were traveling with my wife I would spend whatever on a hotel room. Sign me up for the Waldorf Astoria if that's what she wants.
The issue is I'm traveling with a buddy of mine. It's a friend who likes to drink, drink, drink some more, go to the strip joint, get something to eat, and then start drinking again. We will be in the hotel room to sleep only, and we won't be sleeping much in NYC. I just can't see spending $500 a day on something I'm not going to use.
I've stayed at the Pennsylvania Hotel before. It's pretty skeevey, but I'm not above it. I've heard they have a huge problem with bed bugs though. Obviously you came away unscathed....