I think it very likely Apple have all kinds of 1, 2, 5 and 10 year road maps for all their products (software and hardware).

Given that almost all of them rely so heavily on Objective-C, I expect they've had a road map for that (and XCode and the whole tool chain) for a very long time.

Given the plan is now to phase out ObjC and replace it entirely with Swift, I think it's extremely unlikely Steve didn't know about it, and endorse it.