Daughters 9 and still occasionally sleeps with a stuffed animal.

Im 41 and I have a huge squishmellow pineapple I sleep with.

The stuffed animal is fine! Especially if he's a side sleeper and is using it to prop up his arm and shoulder for a comfortable position. I use a pillow for that, myself.

His home got torn apart in the divorce, of course he's stressed out. I grew up in a dysfunctional home and I still have my stuffed animal from the late 1970s. I don't sleep with it or anything, but I still have it around, sitting on a shelf. It meant a lot to me back then when things weren't good, and I did sleep with it on my bed. Back when things didn't feel stable, normal, predictable. Let him keep it.

Both of these are perfectly normal. My oldest stopped wetting the bed at night when he was 7 - he's a really heavy sleeper and his body just had to grow enough to be able to hold it in. He's 13 now and still sleeps with a bed full of stuffed animals, although he does clear them off if a friend is coming over.