New York (at least much of Manhattan) is not a particularly good place for Uber because the cabs are easy to obtain and plentiful. When I worked on Wall Street we also used the gray cabs. Once you get into the other boroughs even it's a different story. Uber is a definite win in places like Brooklyn where you're not going to find medallion cabs wandering around looking for fares.
In towns like DC where the taxi service is horrendous, expensive, and corrupt, Uber if fantastic. I'd take an Uber over taking a DC cab that's standing right in front of me.
In New York City's "outer boroughs," what denizens call "car services" (livery or "for-hire" cabs) have always been the most common way to buy a ride. Livery cab companies, their cars, and their drivers are TLC-licensed; but their drivers and cars
usually aren't allowed to hack. The cars also lack taxi meters and the drivers are allowed to charge whatever they like for a trip as long as they state the fare in advance. Most of the "companies" merely provide dispatch services. The drivers usually own their own cars.
The cars are not the newest: Most are former yellow cabs that exceeded mandatory retirement age for that work, and so were repainted any color other than yellow (but usually black) and put into livery service. The requirements for a for-hire driver's license are slightly different than for a hack license, but still include a background check, medical exam, drug screen, and TLC-approved driving course. Drivers must display their licenses in a location visible to pax. The cars must carry commercial insurance.
Other than the livery cars usually being old, worn, and creaky by the time they enter that service, I'm not sure what advantage Uber would have over them. At least in a livery cab you know up-front exactly how much the ride will cost. You can also call one using your phone. You just have to use the voice service -- you know, the one where you actually talk into the thing.
I really can't help but conclude that Uber's popularity (at least in NYC) is really based around the app. It gives people another way to use their
toys phones and feel cool. And hey, more power to them. Competition is always a good thing. I do, however, think that Uber should come under the same rules as more traditional "car services" both to level the playing field and for consumer protection reasons.
As for myself, I doubt I'll ever use Uber or Lyft when I'm in New York City unless a companion is paying for the ride. Their coin, their choice. Yellow cabs and car services have worked just fine for me for a very long time. They also are cheaper than Uber in New York City; and the TLC regulation, licensing, and insurance requirements provide some measure of consumer protection.
Rich