Ahhh I know what you mean.
My son, Brody turned 1 on December 1st, and he wakes up three times in the middle of the night. He just wants to be held by me. He is soooo attached to me. He won't let his Dad or anybody else hold him in the middle of the night or basically any other time for that matter.
We usually watch a movie or a couple cartoons around 8p, so at about 930p he's falling asleep or already is. I lay him in his bed, he goes right back to sleep and is fine. But then about 1 in the morning--he's crying. I - like you - HATE having my child 'cry it out' It upsets me and my husband to hear him cry and see his little face all red and eyes filled with tears. It also wakes up my 3 year old daughter. So when he wakes up---he doesn't want to eat or anything, he just wants me to rock him back to sleep! So by 2a he's back to sleeping, I lay him down, and at 330 he's awake AGAIN. I rock him back to sleep, and by 7a he's up for the day! I am pregnant again, and due this summer and I pray to God that Brody is sleeping through the night by then. Otherwise this Momma is getting ZERO sleep.

Have you asked your child's pediatrician? My daughter was terrible at sleeping for naps & during the night. He told me to get her ready ( whatever your routine may be) and lay her down. Let them cry for 5 minutes, then go in lay em down, an only stay for one minute- DO NOT PICK UP YOUR CHILD! then for 10 minutes, and 15 minutes & 20 minutes. (do this for the first few days) then after day 5 you can increase it to up to 30 minutes (if needed) but i never had to go that far. maybe try some cereal to give your son a full belly?