Another one here who had all or nothing feeders at night. Managed to feed them both well beyond 2 1/2. DD1 was a lot of screaming, DD2 not so much. DD2 was the heartbreaker with it though, as she would still ask once weaned and could articulate it very well. With DD1, once she was weaned it was she forgot she ever breastfed.

I so wish I had some answers for you, but sadly I don't. The clingness takes time and the feeding at night is sometimes about comfort not actual feeding. I remember one night with DD2, she pulled off as "boobie empty" then a few minutes later went to latch on again. I told her "but you said boobie empty", to which she replied "Boobie my lollipop".