So with #1, that's the Boston's right. But it's not what the C&D is about, so we should set that aside. This is about #2.
With regards to #2, it's clearly reaching. You can make an argument that they're "measuring the distance with the iPhone", but clearly they're measuring it with GPS. The iPhone is not a measuring device. If they used the accelerometer in the iPhone to measure distance, it might be a fair point.
If they don't want GPS used in commercial transactions it's within the city's power to ban it. But that's what they're doing: banning the use of GPS in commercial transactions. Not banning Uber's iPhone app.
I don't think the city is willing to do that, since this is really about screwing with Uber using whatever regulation they can find and not about fairly enforcing the rules.
Yes and no; the location accuracy of a GPS receiver is strongly dependent on the accuracy of its timing source. The Dept of Weights & Measures generally certifies the accuracy of each physical device. In theory, the drivers could get their phones certified for measuring location and have one of those green stickers on the back that one of the other commenters mentioned.
In practice, any driver that tries will probably find it basically impossible to do, as I believe your analysis of the city's motive is correct.
With regards to #2, it's clearly reaching. You can make an argument that they're "measuring the distance with the iPhone", but clearly they're measuring it with GPS. The iPhone is not a measuring device. If they used the accelerometer in the iPhone to measure distance, it might be a fair point.
If they don't want GPS used in commercial transactions it's within the city's power to ban it. But that's what they're doing: banning the use of GPS in commercial transactions. Not banning Uber's iPhone app.
I don't think the city is willing to do that, since this is really about screwing with Uber using whatever regulation they can find and not about fairly enforcing the rules.