He Cried Himself to Sleep

Usually when Isaiah is sleepy, I pat my baby's back & sing to him, and he goes swiftly to sleep.  I love doing it, lying next to him; it's just a moment that we have that's only ours.  Marcus can't do that.  It's hard for him to be soft & soothing, and he can't sing.  The few times he's tried have been funny because he will make up a song, soften his voice & try to sound like me. 

One night Marcus decided we were going to try the cry-it-out method.  It was really hard.  But it worked.  After that, shortly after putting him down he would play himself to sleep.  We only had to do it once. 

Since then, occasionally, I would still lie next to him & sing to him until he slept.  It's just so rewarding to see him look intently into my eyes, captivated, until he can't keep his eyes open anymore.  And then sometimes, he would still play himself to sleep. 

Recently I've noticed that he sleeps better by himself, so I've decided to let him sleep in his crib more often. 

Also recently he started rolling over again from his stomach to his back, and that just throws everything off for him.  Since he hasn't figured out how to roll over the other way, he gets soooo upset.  And when he's playing himself to sleep, that means practicing his new rolling over trick & getting upset.  How do you fix this?

Tonight I decided I would see if he would learn to fall asleep again by himself.  Even harder this time because Marcus went out with his cousins.  15 minutes in I heard silence followed by a horrible wail.  I buckled and went in & turned him around & put his pacifier in his mouth.  It took everything to keep myself from picking him up & soothing him.  But I refrained.  5 minutes later, silence for 1 minute.  Another wail, silence, another wail, more cries.  Half cries.  Like half sucking, when he's asleep but still wants to nurse.  Silence again. 

I feel like a horrible mother.