Well, last night was both encouraging and a total failure. After his 25 minutes of crying, Gage fell asleep. I went to check on him, and accidentally woke him back up. I picked him up and cuddled him, and he went right back to sleep. I held him and rocked him for 20 minutes, and then laid him down. He awoke briefly, and then fell back asleep - a good sign! He slept from 8:10 to 10:10, when he awoke crying. I cuddled, rocked, and breastfed him off and on for another two hours, but I couldn't get him to stay asleep. At that point, it was after midnight, we all needed solid sleep, so I took him into bed with us. He slept until 7:30 this morning.
I'm not starting naps alone until next week; I feel it's vitally important that he has quality of naps this week to avoid overtiring. So tonight, after we went to free pancake night at IHOP (please don't let your jealousy of my exciting life get to you) we came home and started bedtime a little later than I'd hoped for. It is now 8:49, and after 20 minutes of rocking, breastfeeding, and cuddling, he was still refusing sleep. So I told him it was time for bed, and lay him down.
In 13 minutes, he stopped crying. I am not going to go check on him tonight, because I don't want to risk awakening him again. He's been quiet approximately 10 minutes. He does wake up and fuss a bit, but I am hoping that he'll go back to sleep and stay asleep in a comfortable position. We shall see what the remainder of this night holds for him and his sleep training. I so badly want him to learn to sleep all on his own. I wish we'd have done this when he was an infant.
Update: he would not calm down and go back to sleep. So I'm trying to cuddle/rock him back to sleep then I'll lay him down. It is 9:34 right now so we'll see!