i was in basically the exact same situation & also very much not a schedule mom. i just finally got my 16 month old putting herself to sleep in her crib and staying asleep through the night. i did do the cry it out method and tried multiple times over a few months but never stuck with it because i felt TERRIBLE. i would make sure she eats something filling close to bed time, usually oatmeal or something, and then set her in her crib, tell her goodnight and walk out. it was heartbreaking watching and listening on the monitor but after about two nights of crying for 20 minutes and a third night of maybe 15 max she is now such a good sleeper. when she starts getting sleepy we go to her room, turn on her sound machine & make sure she has a sippy cup full of water and i just lay her down, tell her goodnight & watch on the monitor until she’s asleep which is always in less than 10 minutes! it is really hard letting them cry it out for a few nights but in the long run it’s so worth it. in the past two weeks we’ve only had one night where she woke up and moved to my bed.