Cry it out method

Has anyone done the cry it out method on their 15/16 month old? He’s always slept in his pack n play in my room and would go back and forth between that and my bed through the night and sometimes would just cry unless he was being held or laying with me. We moved right after he turned a year and a part of his crib got damaged during the move and at this point he knew how to climb out of his pack n play so I just put him in bed with me until we got money for a new crib. Well we just got one and he does great during the day for his nap, but when I’ve tried putting him in there for bedtime he just screams and cries. I try letting him cry it out, but then I give in after maybe 10 mins. Is it too late to try sleep training him? Has anyone else done this to their child around his age? If so how long did you let them cry for? Did you go in their room at all while crying? Did they wake up multiple times crying throughout the night and if so how did you handle it? Any help/advice would be appreciated!