D.D.
I'm a mom of a 13 mnth old girl, I stayed at home with her for the first year, I was always told that when baby slept you slept, so I took full advantage, when she would nap we would nap together on the couch. She would sleep in her crib if I rocked her to sleep or if I let her lay on my chest.
I had to go back to work FT and my daughter had to go to daycare, unfortunatly most providers aren't going to hold your child if they have other children ( at least my ex provider didn't)
We slowly day by day put her in the pack and play to take naps yes she screamed and as the days progressed she screamed less. We have also started putting her in her crib at night to fall asleep on her own, once again she screams, but it got shorter and shorter over time.
Now she will lay down for nap and bed time by herself, with little fussing.
My suggestion would be to slowly put him in his crib tell him its nite nite time give him is security is Blanket, pappy, music and walk out of the room , if you have to go back make sure you lay him down tell him again its time to go to sleep and leave the room. Everytime that you think you might have to go back in the room make it longer everytime, he will eventually get used to it. It make take several nights but he can do it. If you know that he is feed, dry and he is not in any danger he will not hurt him to cry. He will be fine, it will be hard but it will make it easier for you and make him more of a "BIG BOY"
Hope this helps. Sorry for the long suggestion, I'm a detailed person.LOL