Sleep Learning: Day 2

It is Night Two of "Sleep-Training". I hesitate to call it "training" simply because it seems to have so many negative connotations with it. Sleep learning is more like it. I want to help my son learn how he can sleep best to achieve maximum happiness... and to be honest, to help me achieve maximum rest and happiness as well!
Last night was awful, for him and for me.
I suppose I should give a little background into our situation. We bought the Arms Reach Co-Sleeper to use before our little one was born. Day one home from the hospital he only slept half an hour in it. That was only the beginning. He gave us troubles from then on. He wouldn't sleep on his own in there. My husband and I spent the first month of his life taking turns holding in the rocking chair through the night. This, obviously, could not become a trend. I definitely did not want him to become dependent on our arms for sleep. We started trying the co-sleeper again. No luck. I was exhausted, sleep-deprived, emotional and starting to battle feelings of depression and even resentment toward my son. I knew this couldn't continue. Out of desperation we took our little bean into bed with us. And he slept like a charm, the first night in bed with us at 4 weeks old he slept five continuous hours. I was amazed, so we decided to give it a go.
Every so often we would try to get him to nap in his co-sleeper though, to no avail. We did all we could, thinking he liked the smell of our bed, but that didn't seem to be the issue. I had put my breastpads, t-shirts, stuffed animals or blankets that I slept with, all in his bed (nowhere near his head, mind you, and he was swaddled so there was no chance of him grabbing them) - and he wouldn't have it. I finally concluded that perhaps his bed is too firm. Indeed, the "mattress", if I can even call it that, is merely a board with some crinkly plastic, about 1/2" thick. I wouldn't sleep on it either! Our mattress, however, is a cozy pillow-top. You can imagine why he might prefer our bed - even without us in it!
He is now 14 weeks old (just over 3 months), and I am ready for him to move out of our bed. I know it's only been a little over two months of him sleeping with us, but I miss my husband, for one, and for two, I want to help Cobi develop healthy sleep habits. Given that he is still young, now would be the ideal time.
Given that background, it brings us to yesterday. I laid his crocheted afghan and quilted minky blanket underneath his sheet to give is some extra cushion (but not too much) and we started his bedtime routine.

Night One: I forgot to keep track of minute by minute, so it will be more of a synopsis. We completed his night routine, diaper, pajamas, swaddle, and night nurse. I lay him in his bed awake. He immediately starts crying, so I give him his pacifier. He can see me sitting on the bed next to him, but that seems to make him more upset as I'm not actually picking him up. I wanted to give him five minutes before giving in. He looked so hurt that I wouldn't hold him as he cried. It was very hard for me to hear him cry like that. After five minutes, I hurriedly picked him up and soothed him. He was so mad, he kept crying, so I nursed him again and he calmed down. Such a little boob man! I continued this pattern for about an hour, lay him down, pick him up. I tried letting him cry on his own in hopes he'd fall asleep after a few minutes, but that didn't happen. Every time I left the room, I started bawling. I felt like a bad, horrible mom. I couldn't stand it. Eventually he fell asleep with me holding the pacifier in his mouth. He only slept two hours in his bed before waking up crying. My poor baby... and poor me. I knew this is NOT the way I wanted to go. I was able to get him back into his bed after nursing him to sleep, but he was only asleep again for two hours, I gave in and let him back into our bed. I didn't have the energy or emotional capacity to wrestle with him.
Night Two: I decided to try it a little differently tonight. I wasn't going to let him cry, even within plain view on me. I really wanted a gentler approach and given the emotional trauma I suffered yesterday, I knew I needed it to be a kinder approach.
6:22 - we start Cobi's bedtime routine. I carry him upstairs, "shushing" and patting his back to signal it's night time (this is actually new, I'm hoping it helps prepare him and allows him to read signs of night-time). I put him into his night diaper and pajamas and sing while I change him. I bring him to our room where we turn off all lights except the night light and draw the blinds. I swaddle him in his summer infant swaddle sack, and nurse him on our bed. He is getting drowsy. I burp him, and whisper "good night Cobi, mama loves you. Sweet dreams."
6:40 pm: I lay him in his bed, awake, but obviously tired. I walk away so that he can't see me, thinking that maybe last night he cried because he could see me and I wasn't picking him up. I was going to let him fuss and squirm, but not cry.
6:49: his squirming/fussing turned into crying. I pick him up and shush him, he smiles at me. I totally just got played!
6:53: lay him back in his bed and whisper goodnight.
7:00: Cobi starts crying again, I pick him up, sway him in my arms. He is obviously fine, as he stops crying the moment he's in my arms, and immediately closes his eyes and is nearly asleep.
7:03: Lay a near-sleeping baby back in his bed, he has his pacifier and is sucking intermittently.
7:09: Pacifier falls out of his mouth and he cries. I pick him up and rock him in my arms.
7:13: Back down in his bed, he is very sleepy.
7:15: Crying again, more rocking.
7:17: back in bed.
7:20: Crying again, shushing, kissing and swaying.
7:23: I hold the pacifier in his mouth for him while I lay him down, he sucks very slowly, he is mostly asleep. I leave the room and let him be. He is quiet.
It is 7:41, he is asleep. Let us see how long it lasts.

Until tomorrow! UPDATE: 7:57pm he woke up crying, I picked him up, and rocked him downstairs in the rocking chair. 9:13pm: asleep in his bed again