I don’t know the Rov, but its possible that from the way the question was posed (both then and now) the question indicated the answer the person wanted (needed?) to hear.
On a situation that can go either way, a smart Rov will make the call as he sees fit for that instance.
Had the question been, “is pork kosher”? the answer would have been no both times. The “work/learn” question has so many variables, its impossible to have a “one size fits all” answer.
Kinda like “other” rov shailos. To the same question,one person gets a yes, the other gets a no. And both are the correct answers. That’s what rabbonim are here for.