Well it doesn't really sound necessarily like ocd. The door thing may be because he can hear, smell or see something you cant. Callie (my yorkie) will cry for many reasons and not necessarily where the problem is like if she wants someone to sit with her she will cry sitting in random places of the house. Do you see anything noticeably wrong with his hinny when he is chasing his tail? Maybe his hinny itches or a little tiny piece of poo poo hanging off of it? Also Welcome to yorkietalk