Maybe the tail chasing is for fun or he does need his anal glands expelled. My groomer does that for me. It wouldn't hurt to ask them when he gets groomed. Calleigh does throw her food in the air at times too. She seems to be playing. She will also take a mouthful of kibbles at one time and go to the dining room to eat them. I guess they all have their little quirks. We have been so housebound with all the snow. I guess I can expect her to do crazy things..
You have a darling pup!