TL;DR: Uber is innovative, but their approach (or lack thereof) to dealing with regulatory hurdles in each city disgusts me.
It seems like HN has already picked up on the major issues Uber faces in Boston, as well as pretty much every city: a new style of relationships with drivers, and "metering" virtually-on-demand livery rides, which are intended to be both unmetered and pre-arranged.
After seeing this same story repeated too many times now, and the resulting discussion, I feel the need to throw down. You don't need to trust me (IANAL, etc.), but based on my experience in the field -- I co-founded HireWinston (initially a Canadian, corporate-focused Uber competitor; we've since pivoted to competing indirectly by selling taxi fleets) -- I hope I have something to add.
First, the relationships with drivers: Uber tends to work directly with drivers (many, if not all, of whom they hire legally from existing livery services). In order to boost their chances of availability, they spend some of their hard-raised cash to book drivers for entire days, taking a steep loss at first in the hopes of driving enough demand to better satisfy their capacity.
In most cities, there are clear regulations that define a livery service. We found that, if you work as many commenters understand Uber working -- namely, as a network that has pre-arranged agreements with drivers or livery services to shuttle rides in their spare time -- you're in a sufficiently comfortable area not to get shut down. However, the way Uber works to juice supply (especially in newer markets) tends to clearly fall under the definition of a livery service, as they have their own "employees" that they pass rides to.
Second, the meters. This one I'm much more in their favour on: the phones themselves are not metering devices as the laws define them (i.e. they do not themselves calculate the price). I haven't personally torn into their source code, but having heard from an insider and having built this tech myself, I'm fairly confident their Driver App simply sends GPS data back to the server, where the calculation takes place according to a pre-defined rate. The customer either implicitly or explicitly accepts this rate through the TOS and/or by virtue of using the service (assuming the rates are published somewhere).
This setup guarantees they have something to show regulators if ever asked. From our research and testing, the integrity of the data from existing metering technology is similar enough to that from an iPhone or Android's GPS (ideally accompanied by accelerometer data). And, since the calculations happen on a server that records full route information rather than in a black box that discards it: way easier to share this with regulators. So A+.
Third, and most importantly, is what you don't see: Uber's relationships with city regulators. In Toronto, the municipal government sent us an official notice that they were concerned with our business, and that they wanted us to come talk through our business model and underlying technology with them. They were genuinely excited that there was innovation happening in the field in their city, and really just wanted to make sure we weren't doing anything egregiously wrong.
We sat down, and had an incredibly pleasant meeting. 30 minutes, back-and-forth Q&A, with some regulators who have spent years in the space. They appreciated that we knew the laws, had worked to abide by them, and were comfortable with all but one aspect of our business model (cancellation fees). No C&Ds were sent out.
At the end of the meeting, they asked us what we thought of Uber. Apparently, for months, the Uber team was dodging any request for a meeting the office sent them. While I definitely cannot attest to Uber Boston's actions on this front, I can't imagine that Uber Toronto was taking their plays from a different playbook.
In summary: Uber has done a tremendous job pushing the industry forward, and I'm confident that our approach -- selling the underlying software to existing taxi fleets, who truly want to better service their customers but have no idea what to do with technology -- is a more sustainable and dependable iteration on the model. I'm thankful to them, and I truly love a lot of the folks I know who work there.
That said, I have no sympathy whatsoever for these C&Ds whenever I read about them. The company relies on deep pockets and public sympathy for the "underdog technology company" to change laws, rather than working with the existing system. And, frankly, normally I'd even be fine with that... if it weren't the taxi drivers -- the most marginalized members of the entire taxi ecosystem -- who were getting the shortest end of the stick.
DISCLAIMER: I do not, and have never, worked for Uber. Most of my knowledge comes from a mix of an outsider's view and third-party testimony of the approach that Uber has taken in Toronto and NYC. I'm not sure if Uber Boston took a different approach than Uber Toronto or Uber NYC, so take all specifics with a grain of salt.
(edit: formatting errors)