NY is stingy about such stuff without any reason really.
Two things:
1) Wires don't care about the direction of power flow, and neither do transformers.
2) Many circuits have been upgraded with sensors and automatic switches/breakers making real time monitoring a breeze.
The subs won't care either. If you have have 1800KWs of generation being injected at various points on a circuit supply 2000KWs of customers the substation transformer will be much happier being loaded to 400kw instead of 2000kw.
That will be the hard part and where technology will have to step in.
A cloud going over can certainly cause a noticeable drop in feeder voltage when the solar makes up more then 20% of the generation.
Ideally something in real time will have to prop the voltage backup up, and then back-off in equal magnitude and speed when cloud floats away.