Hi,
I do not know how the rest of your day looks like, could you provide what happens after 9 am when he wakes up? It can help a lot to get the whole picture I think.
But to be honest with you, I think he needs a little more A time. Sometimes even if they seem tired, increasing that first, morning A time can get the just tired enough to take a good sleep.It can also shorten the whole falling asleep proccess. Look into here:
Average A times- BOOKMARK ME! That being said, what if you moved that 8:40 to 8:45?
Question about WU 7am. Is there a reason you wake him up at 7? Family errands, walking kids to school etc?
Also, I would not advice you trying to resettle for more than 20 min. At this age it can irritate LO a lot and ofcourse after 40min of fighting sleep he will fall asleep. By giving him 20 min to fall asleep again you're sending a clear signal " Ok, I get the message. You don't want to sleep anymore." What I am trying to say is, if yuo see resettling is not working after 20 min just start another EASY cycle, but maybe wait with E a little.What do you think about it?
Lots of kids are tummy sleepers. As long as he can roll over back and forth, he is fine. But ofcourse, you know best, what you're comfortable with and feel safe with. If he likes the cloth that's good. There is nothing wrong in it. I would let it be to be honest. Try removing anything else from the crib that he doesn't pay attention to, extra toys, pillows, blankets. These are the most dangerous.
Let me know your thoughts