O.G.
i owuld wait until he starts to climb out of his crib. my daughter was about 20 mo. when we put her in a toddler bed. my son is currently 14 mo. and has no desire for the toddler bed other than to play in it. he climbs on his sisters bed and lay down just for a second then he is up again waiting to see if you are looking before he gets down and starts playing with toys. as far as the pillow goes my son has had a pillow since he was 9 months but he never sleeps on it he like to lay up against the pillow i think he likes the feeling on his back. it all depends on your preferance dr. dont recomend pillows until a child is 5 but both of my kids had them early on but i also never worried about what might happen. as long as you are confortable with it then you could give him a small pillow.