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How many naps?!
My DD is a smart kid and when we would go get her MOTN around 16 months it is a no go to go back down and she ended up in our bed, I never did CIO, so it might have worked, she still at 2 will wake MOTN 2-3x a week but now it is to pee!
I'm so sorry!!!

@MrsADS: no eye roll I rocked or walked my girl down for naps until like 16-18 months I was PG then and now I still pat her back

@gingerbebe: @MrsADS: I too was going to ask what time bedtime is. If wake up from nap is 1:30 then I would say bedtime should be 6/6:30 at that age, at least until you can push his nap later. It's common that when you get to one nap you need a crazy early bedtime. But it's temporary!
If bedtime is at 7/7:30 or later, I would be inclined to say that overtiredness is at a minimum contributing to the sleep issues.

Also agree with @gingerbebe: that somewhere in that age range there is a regression. My son was sttn with very few wakeups from 5months till 17/18 months. Like maybe once every other month if he was sick. When he hit that 18 month regression he was waking once a night 4-ish times a week. Yours could be hitting earlier and with a vengeance since it sounds like he isn't much of a self soother.

Overall agree with everything @gingerbebe: said.

@MrsADS: Ah yeah, see I would look at it this way - if he can't make it more than 5 hours from morning wake up to nap time, then definitely don't do more than 5 hours awake from nap wake to bedtime. You answered right there that you know his threshold for wake time.
ETA: my 2y4mo still can't really do more than 5/5.5 hours awake at a time. I can mayyyybe stretch him to 6 if I really have to and there's enough distraction (like we're at a party). And actually he's only awake 4-4.5 hours from nap to bedtime. Some kids are just higher sleep needs and maybe your son is too!
I would also say that he should be in the crib by 6:30, not starting routine by 6:30. I know though that that can be tough if you WOH. I did for a while and I just told my boss "look, I have to leave at 5pm. My kid goes to bed at 6/6:30. The end." But I was in a flexible situation.
Is t possible for your sitter to at least start bedtime routine or at least give him dinner so that you can take over and hopefully have some quality time before bed? It might be short, but a sleep specialist once told me to think of time with LO as quality over quantity. If they are cranky and overtired and everyone's sleep is impacted, no on wins so put them to bed early and make up for it in mornings or on weekends.

I know it's not easy! Hoping you find a solution that works well for all of you! xo

I'm so sorry. Does he ever play in the crib during the day? That makes it less scary.

My son is a horrible sleeper. I just have sympathy.

@MrsADS: FWIW switching to a floor bed helped. I started nursing and rolling away, then nursing in a chair and then putting DD down and patting her back while I sat on the bed. Now I'm sitting next to her but not touching her while she happily sings herself to sleep most nights. Little steps. Little steps, a nightlight, and an earlier bedtime.

I'm really sorry you're going through this. I think in terms of triage, you just need to get him to sleep however you can. He's basically lost his mind because he's so chronically tired. Perhaps you can talk to your pediatrician - I think a few moms on HB had their kids on melatonin for a few weeks as a "reset" to the sleep cycle.

Do you have a video monitor? Can you watch him on the monitor to see how he's doing? I don't think kids really stop breathing because of crying. Throwing up would be unfortunate, however. We always double bagged his mattress (mattress protector, sheet, mattress pad, sheet) so we could quickly clean up when he threw up (he did all the time from reflux). I don't recall if our son puked while sleep training, but that's how we would have handled it.

We ended up doing extinction because our son got FURIOUS with checks and every other gentle method. He is also very, very stubborn. But we decided to go this way because was SO chronically overtired from months of colic and reflux screaming that he was literally delirious crazy. I think the first 3 months of his life he mostly slept in 20-30 minute bursts 24 hours a day. Once he was actually sleeping normal hours, he was literally a different person.

What is your DH's tolerance for CIO? Can he take lead? When we sleeptrained our oldest, my DH handled the brunt of it. I couldn't really deal with listening to him cry (my son blew out my eardrum when he was first born, that's how loud he was, and he was colicky with severe reflux and did not stop crying for like 4 months. To this day when DS1 has a really hard crying fit, it gives me a PTSD anxiety flash back to his infant days). DH would just stay up and watch him on the monitor and sit through the screaming while I was like holed up somewhere with lots of white noise and ear plugs hiding.

What I will say about CIO is please don't do it if you wont be consistent about it. Its not fair to your child to make them cry for 2 hours and then give up - it just makes them cry louder and harder because they think that's how they will get you to come to them. So if you're really not comfortable with CIO, that's totally okay, but just don't do it until you commit to giving it at least 5 days or a week or whatever timeframe you agree to. It sounds like attended CIO and checks aren't working, so you're left with extinction. Unfortunately, extinction works because the kid learns you're really not going to come back even if they cry really loud and that they have to go to sleep. So until you're ready for that I'd say you're just going to have to do the best you can to get him to sleep however you can.

@MrsADS: what time does he typically fall asleep? Because if it's usually around 9 I think he is going to scream if you put him down at 7. There's a post on precious little sleep about this but basically you put him down at the time he's usually falling asleep then work on pushing that back to abnormal time

@MrsADS: Kudos to you for not losing your Sh** Keep It up Mama!

@MrsADS: Oh, and I also want to add that you should give the routine a solid two weeks of consistency. Pick your routine and stick with it, just like the sleep training it's only effective if you remain consistent for a reasonable amount of time. Kids always have an adjustment period. And I was told by my pediatrician to give everything two weeks before throwing in the towel and changing My approach. If it doesn't seem to work in the first two days, don't go and change it up.
This is just one of those things in parenting that is so hard to get through and it's so hard to remain consistent, but it's something that will pay off in spades.
Is hiring a sleep consultant a possibility at all? I live in New York where they are abundant, but I'm not sure if you have them where you are. Here they will actually come and sit with you through the sleep training to help you remain strong and to reassure you. And I'm sure there are some who would respect that you don't want to do CIO. Or they may observe and tell you that extinction CIO is the only option. And hearing a professional's opinion on that might help give you the nudge to do it.

@MrsADS: what about books about bedtime? We have a "Night Night Elmo" book with flaps that my son likes a lot. It goes through the routine of bedtime and shows "what's next". I'm sure there are tons of books like this.
Also, no idea if it actually works but we've been using Johnson bedtime bubble bath for a long time. And I will sometimes play soft music (I like a bedtime prayers album I downloaded but could even be classical music or another secular bedtime album). Nothing exciting or upbeat.

I agree that talking him through and narrating steps and talking about what's next is good. In anything, really! I do it even when we're going to run errands. "Ok son, we are going to get in the stroller. Then we will go to the bank and the grocery store where you can pick out fruit! Then after our work is done we can go to the playground". I specifically name it all and explain the "reward" at the end (playground in this instance) and it really helps him.

@MrsADS: Hurrah! I hope he sleeps well tonight. I think if you can get a solid bedtime routine, then you can tackle getting him to sleep independently and/or an earlier bedtime. Congratulations on the first night of the first step!

@MrsADS: Great job! I second everything @Dahlia: said. He went to bed with zero crying - that was the first hurdle. A solid bedtime routine is key and yours sounds perfect. Do it exactly the same each night for at least 2 weeks.
Once you reset his sleep and he's more refreshed you can work on everything else.
How did the rest of the night go?

@gingerbebe: yes to lights being off when we go into his room, even hallway/kitchen/etc. and also TV. I didn't want him to think he's missing out on something fun if he cried and we open the door to go in (even moreso because we're in an apt and his room is off of the living room and across from the kitchen).

@Dahlia: so true! We even say bye or goodnight to TV characters when it's time to turn off the TV. He does it and doesn't complain!