Staying at a bad W (Chicago Lake Shore) is a total waste of money.
If you think Lake Shore's bad, I recommend you stay away from the New York ones!
I've stayed at a few W's (Barcelona, Lake Shore, Boston, Seattle, NYC Lexington, NYC Union Square, Mexico City, South Beach and Dallas) and the only ones I've ever been disappointed by were the NYC ones. Tired, old, dolled-up hotels trying to make something hip out of something that isn't. Sure there are some OK elements (Underbar can be fun) but overall, I'd rather stay elsewhere (Le Parker Meridien, for example).
The standouts for me are Barcelona (I was the second or third person to check-in, ever

), Miami Beach, Mexico City and Dallas (Dallas because of the rooftop bar and the upgrades, not because of the location!) Boston is pretty nice too, though in a quiet/boring area.
Very nearly booked the W Maldives too, but just couldn't justify an extra $2k for 6 nights over the place we did end up booking, which by all accounts looks incredible, with much bigger villas/bungalows.
Cheers,
- Febs.