Also, in conjunction with the good counter-points being made by others here, let's not forget his points rest upon free money. Without that bonus, he'd be a dollar short, not 5 cents. In fact, with option 3 (the $39 one), he literally received an extra subsidized ride. $39/2.5 is 15.6 => 15 rides. But with the free bonus he is able to take his 16th ride.
I suspect this has more to do with poor UI, than anything else. Take a look at the Citibike UI if you're not an annual member. You will have less hair after having used it. Makes the MTA one seem glorious.