Earlier quoted context omitted.
In addition to ads on their web properties, they still have a sizeable (though aging) userbase that they milk for unnecessary services. I cancelled my mom's AOL subscription years ago and they were charging something like $25/mo when the only thing she used was their (free) email service -- though of course during the cancellation they touted things like antivirus and ID theft protection that she apparently had acces…
"Unexamined legacy subscriptions paid without a thought," is another way of saying, "Has too much money." If this is a widespread Boomer phenomenon, it explains a lot. I still kick myself for spending 6x MVNO pricing on my cell phone plan with a legacy carrier whose features I didn't need.
That business model is what a lot of tech companies actually bank on that why they require a credit card on a free sign up.