Can I ask what's going through your head while you're waiting for him to go to sleep? What are you thinking? What do you expect to happen? I know anxiety is AWFUL and I certainly don't want to in any way take away from how stressful this is for you. But as an outsider, I have to say that I think your DS sounds like he settles beautifully! Well done! It's fantastic that he can 'chat' himself to sleep. I rocked DD for 18 months (if I hadn't she would have screamed the walls down) and even now that she can 'sort-of' self- settle at 20 months, we often face 1-2 hours of silliness and mucking around before she will even consider lying down and trying to sleep.

So that said, I think your solution here has gotta come from working on what makes you feel so awful while waiting for him to settle and finding ways to detach and soothe yourself. Good luck hun.