R.C.
I tried the "crying to sleep" with my first child. It did not work, for me or for him. I couldn't bear to hear him cry. I am a firm believer that little babies cry because they need something, even if it's just so their mommy will hold them. Babies need to be held and reassurred. They need to know that when they cry, you will be there for them. Crying is the only way they can call for you. I held all of my children when they were babies. I held them until they fell asleep and then put them in the bed. Or I would lay next to them for a while until they were almost asleep (when they got a little older). They are now 10, 6 and 3 and have no trouble at all going to bed on their own. They get in their beds awake and go to sleep on their own after I tuck them in. They all sleep through the night and only come running to me when bad weather (very loud thunder and bright lightning) wakes them. I don't think your child will be a terrible sleeper if you hold him until he falls asleep or rock him or whatever you do to help him fall asleep. Consider this a bonding time for the two of you. They aren't little babies forever, they grow up so fast. So take advantage of this time and get in all the snuggling you can. You'll be glad you did.