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I wish I had a ton of advice but I feel like I'm failing at the whole routine thing. I have been starting small with bath, feeding and rock to sleep all starting at 8. Nolan fights sleep anywhere but mine or DH's arms so we usually can't get him in the crib until after 11 or 12 and last night he never made it to the crib. he slept with us.
My best advice is to try to work around his natural rhythm. For example - Bodhi is typically ready to go down for the night by 8 or 8:30, so about 7:45 I bathe and swaddle him and then nurse him. He usually passes out on his own. Bourne on the other hand is a late night kid and always has been. He would stay up until 10 if we let him, but we gradually moved his bedtime up and now it is 9:00 pm (he's 2.5) He still doesn't go to sleep until after 10 some nights but he has to be in his bed and quiet by 9. With him we started his bedtime routine around 8 pm. Now he takes a bath, PJ's, watches an episode of Umizoomi or Jake, brushes teeth and then he and dad read a book together and go to bed.
If Jackson dozes off close to the same time during the day, that is probably his nap time, so about 15 min. before that time, feed him and swaddle him and then go through your routine (swing, chest, rock - whatever you do). You will start noticing the same with bedtime at night, too. It won't be like that every night but most nights you will be able to notice a pattern. It may be that he is over tired and not able to stay asleep.
Most babies at this age take 3 naps a day - 2 decent length and one short cat nap. (but not all babies do)
Hope this helps you gain some sanity. Hang in there, it will get better.
Edited to ADD: If it doesn't happen right away, don't give up. It took us until over 6 months to get a consistent routine established with bourne, but it will pay off.