I haven’t lived in NYC, but I have lived in Boston. Isn’t the real concern winter? Has Waymo (or any other self driving tech company) shown that it can handle the snow well: non-visible lanes, downshifting to avoid braking, etc.?
Having a seasonal service is not a bad idea. The big problem with that is cutoff times. Too early and people will complain when they can't get a ride when no snow is on the ground. Too late and you're liable for everything that happens when the road is covered in thin ice or sleet, including leaving someone stranded. You will need very accurate weather predictions for operating over the winter months.
Definitely interested in how this turns out.