I'm a founding member approaching 2,000 trips. Because of bonuses (I've forgotten details), my annual renewal isn't due until early July, and I'm definitely going to re-up. Enough of my trips were in lieu of public transport so, as a value proposition, I've clearly gotten my money's worth. Considering convenience, the real plus for me is no need to clean my own bike after a ride in foul weather. In spite of NYC Bike Share's unnecessary early and often self-inflicted wounds, the service has been (IMHO) wildly successful.

Keep in mind: there's a not heavily advertised 10% discount available on annual memberships paid with a Citi card.