Good or bad for eight month sleep training

Mackenzie

So my son has been super duper bad about sleeping in his crib so my husband and I decided fine when he starts crying really bad at night he sleeps with us usually he fine till about four with ten feeding I know a lot right trying to make sure he full and stuff also. Lately he uncomfortable everywhere except on the couch where he sits upright. Is this normal??? Also my mom and dad both say I should start letting him cry him self to sleep but he gets tired around 10 and usually he takes a nap anywhere between 5-7 so I been letting him cry like yesterday was ten today fifteen tomorrow twenty and so on he gets very red in the face he sleeps in a umm sleep sack and he rolls to his tummy. He does know how to roll back but so frustrated he won’t turn back over I was just wondering if this makes me a bad parent

This is how he likes sleeping and idk why just he sleeps great like this

This last picture probably the most he slept in his crib witch of four hrs no feeding st night