For the mass of a aerosail, you could put a small rocket motor on a satellite and deorbit in a more timely and controlled manner.
For boosters, I didn't know we were still leaving upper stages in orbit these days. All this concern over space junk has been around since at least the 80s, and I know that many boosters do deorbit themselves. Yes, you need restartable jets, but restartable jets are desirable for orbit insertion maneuvers anyway.
I guess you'd have to do a trade study about whether the mass of the extra prop needed to deorbit a given stage is less trouble than the mass, complexity, and bulkiness of an aerosail system.
You also have to study the benefits of leaving an aerosail-equipped booster in orbit for as many as 25 years, complete with the increased collision hazard of a large-area sail, vs. the benefits of a powered deorbit.
You also have to study the risks vs. benefits of funding such a system's development. Will you have to spash out zillions of dollars/euros for a questionable return?
This would be a cool systems engineering problem to work on.