I think some of it might be self-inflicted too rather than purely a scaling issue. Anecdotal evidence here but probably relevant- I got a mail from Uber a while back, where (presumably) some automation noticed that I was taking a bunch of uber rides to the airport when I was in Boston, but never from, so it offered some Uber credit to use from the airport. I was pretty stoked that Uber had such great analytics and this past Saturday, requested an uber when I landed. Once I got picked up however, it was a different story, with the driver claiming I had "tricked him" and that it was illegal for him to pick anyone up from the airport and that Uber had specifically given him guidance not to pick anyone up from the airport. Clearly there was some miscommunication there and although he calmed down once I explained my side of the story, it still creates a bad experience (probably for both the customer and the driver). Uber support was reasonably prompt in getting back to me but it was somewhat of a non-reply and I still don't know if picking people up at Logan Airport is a supported scenario or not. However, my positive experiences with Uber far outweigh the negative ones and I think Uber still has that built-up goodwill going for it which should cushion it through these growing pains.
> and that it was illegal for him to pick anyone up from the airport and that Uber had specifically given him guidance not to pick anyone up from the airport
This potentially has some truth to it. Many times, to operate a passenger service to/from the airport requires the operator to purchase a (costly) license from the airport authority. Depending on bylaws etc, unlicensed operators who provide passenger service to/from the airport will be subject to fines. In other words, providing access to ground-transport operators seems to be a revenue stream for the airport, but also likely serves to protect the air passengers from cowboy/dodgy transport operators outside the terminal.
Anecdotally, I once struck up a conversation with a taxi driver in Sydney, Australia. We'd passed a pedestrian who (for some reason) was standing on airport land, some distance from the terminals, trying to hail the passing taxis. The driver remarked to me that they'd be waiting for a while, as no taxi would ever stop there: Apparently it is stipulated in the contract that the taxi company has with the airport, that they can only collect and drop fares in the designated areas outside of the terminals. If they pick up a fare at any other location on airport land, they are subject to large fines (he said $10k, but perhaps this was hyperbole). I found this an interesting insight into the level of regulation apparently applied to airport ground-transport operators.
