Here is proof that I have been letting him "cry it out."
Last night he woke up about 45 minutes after he went down. He didn't cry a lot but would cry in like 1 minute spurts. I could tell he was still half asleep just by the way he was crying and stopping and crying and stopping. He was really fussy in the evening and Grandma said he only slept about 40 minutes the entire day so I knew he had to be exhausted. We agreed that we wouldn't go in there while he was having these crying bouts. I headed to bed about 11:30 (after the UT/Kentucky game) and he had been quiet for about the last 45 minutes. So I checked the monitor right as I got in bed and I saw the above. He had fallen back to sleep sitting up, leaning on the crib bumper. So sweet. So I left him there. I had to hold back the urge to go in there and gently lay him back down but to avoid waking him, I resisted my temptation. I flipped off the monitor and went to sleep. When I got up this morning I turned the monitor back on before I showered and he had made it through the night just fine. We are so glad that he is learning to go to sleep on his own and our efforts are paying off (as all of you said it would...)
Because he slept so good he was wide awake all the way to Grandma's this morning just talking and singing. He got quiet about the time I got off of 40 at the Chapel Hill exit and I looked back and he was sucking his thumb! He hasn't done that in a while. Then as he was closing his eyes, he switched to his pointer finger. He sucked on that until he fell asleep and it fell out of his mouth, right as I was getting him out of the car, lol!
In honor of tonight's big game I am sporting a new pair of earrings.