i have a small home daycare and each of the children I watch started with me around this age. They were in pack n plays until they totally understood nap time was naptime, no if ands or buts. It will take a little courage and perseverance. The first week will be miserable and the rest of his days will be great. I would make sure there is a steady routine. I put on Sesame street while i make lunch, then we eat lunch, then we wash hands, then we potty/diaper change and then we get our blankies or stuffed animals and get our beds ready. Then I put on soft music and they get in their beds,everytime, it's the same. He may scream and kick and throw a tantrum, for an hour, but eventually he will fall asleep. As long as your caregiver knows he has every need met and is safe, even if she has to put his pack n play in a room so he doesn't have an audience. If he cries, it is because he doesn't want to sleep this way and is trying to cry to get his way. It is sad and you wish everything could be peaceful, but understand that his frustration is because he is worried about what the boundaries are. As soon as he learns that this is the way it is, he will be so grateful to have a routine he can rely on. Each day will be less and less crying and he will eventually beg to go in his pack n play when he's tired. He will appreciate having his own space.