I can almost guarantee you he is on meds, unless he got sides. Although he does have the "f*** what you think" attitude to his appearance, his hair is still a central part of his look. He may not keep his hair groomed and looking nice, but you can tell he still thinks about it.
Your hair looks good as is right now, and although you have receding temples your hairline still looks pretty thick. It is a tough call. It really depends on how important your hair is to you and what you are willing to do to prevent the possibility of any future hair loss. Just taking finasteride would...
I think your crown looks better, but it is hard to tell. Your hairline loss is pretty minor in the first place and I dont see any difference from February.