If anyone can pull off this, it is Apple. They have a very loyal ecosystem developed, one that does not mind spending some money. Compare that to Google which opted to give people stuff, they have much bigger numbers yet fewer willing to spend money.
I am not sure the entire news thing for pay will work in the end since there is a lot of other options developing. Overall, closed ecosystems might have trouble down the road.
RE: Apple is developing a premium news subscription service