The conventional wisdom seems to be (becoming) if you start out offering something for free (as they do now), it's going to go hard for you if you begin charging.
I'm assuming the product in there is good on some level since they have such brand cachet, but I don't care to deal with getting at because it such a pain. If they made it an enjoyable user experience, I would probably pay for it because I know that it is good.
Instead, I suspect they'll simply re-wrap the current app in an ongoing subscription charge and call it a day. Then wonder why nobody bites (aforementioned Safari access will most likely still be there, after all). It's the strategy they chose with ill-conceived (and abandoned) the Op-Ed paywall, and I imagine it's more or less the same path they'll take again because it seems safer to them.