Falling asleep by herself - The first night

Other than a night or 2, Abigail has never fallen asleep by herself. When she was a newborn, she always fell asleep while breastfeeding. Past a year old, she no longer fell asleep while nursing but would eventually drift off to sleep with someone sitting on the floor next to her floor mattress. It would, on average, take an hour before we could leave. This summer, we transitioned her to a big double bed. Since then, we actually need to be up in bed with her. It still can take up to an hour for her to fall asleep. We are extremely lucky if she is asleep by 930 since most nights, it is 10pm. Friends and family have mentioned on numerous occasions to just let her cry. We tried that once (controlled crying for 1-2-3 minute intervals) and it felt so wrong, I promised to never do it again. Even now, I feel wrong letting her cry by herself.

Her lack of bedtime routine is entirely our fault. We have never established a routine. Sometimes we start bedtime at 8, sometimes 9, sometimes we are not even home. We don't give a bath or massage every night. So figuring something out will be the first thing and sticking to it the most important.

So here is the schedule we are trying
8 - snack
830 - brush teeth, wash face, diaper, pjs, read books
9 - lights out.

I will stay in her bed for several nights until she gets used to the new schedule. Then I will sit at the foot of her bed, then on a chair and hopefully make my way out of her room while she falls asleep all by herself.

Tonight, I followed routine and am sitting here, at 10pm, writting this with one hand since she absolutely wants me to rub her back while she falls asleep. She is some lucky we lover her so much!

With a new baby on the way, it would be great I she could fall asleep on her own since I will not necessarily have 2 hrs to just sit with her for her whole bedtime routine. It may take a couple months for this whole procedure to give us a result we want. We are ready. Any ideas or tips are welcomed!