The unprecedented peak retirements taper off a bit after about five years or so, but after that there are still PLENTY of retirements by normal industry historical standards, I think into mid 2030's.

So I'd do everything possible to progress quickly now while all of the movement is occurring just so you don't miss any opportunities. That might include incurring debt which most of us would recommend against in normal times.

Also the retirements will benefit you as a CFI and regional pilot, due to more available students, high job availability, bonuses, and rapid progression in the regional ranks.

But as you said, there's always the possibility of a (another) black swan...