Overtired cycle questions

How long does it take to get out of this sleep debt/overtired cycle?

How will I know LO is in the clear?

Will he ever go back to DWT of 7? I’ll be happy even with 630

Why does this such so much?!

Some context: LO is newly 16mo. Transitioned to 1 nap almost a month ago in prep for daycare, he was also showing some slight signs it was time. Our problem started with early morning wakes. He would wake crying around 530/545 then wouldn’t settle, would be quiet sucking his fingers, playing with his hair. But would be awake tossing around. I’ve tried going in and helping him back to sleep until our DWT of 7 but it doesn’t work. It’s like he gets distracted by my presence. I will be rubbing his back and he will reach around and try and grab my hand, start babbling to me. He’s started screaming at bedtime, and having night wakings.

So I’ve begun starting our day no earlier than 6. So he still is awake rolling around for some time but it’s not 1.5hours anymore - hoping this will help relieve the overtiredness. And he’s getting a bedtime of 6.

I’m not capping his naps and they usually are around 2-2.25 hours.

Our schedule the last couple days as been:

6:00 out of crib 11:15 nap (usually 2-2.25hr) 6:00 bedtime

I guess I’m just looking for reassurance I’m doing the right thing? And this will be over soon? Or if there are any other suggestions on what I could do better. Oh, he also starts daycare in Sept so I’m prepared for things to go off the rails again.