i've seen the entire series probably 8 or 9 times. if you pay attention to the show despite his job as mob boss, tony actually has quite low self esteem. what reason does he have to not have low self esteem? he's fat, his mom was mutually and verbally abusive, and his father loved his older sister more than he loved him.
Tony is the perfect example of a guy who spends money and does stuff so he can feel better about himself.
There are a few on the show who picks up how he ticks and that despite the exterior persona that he is a hurt AFC... his cousin Tony seees right through it as does his shrink and Hesh .
you say that the writers are catering and trying to make him human but in reality, there is nothing really alpha about im outside of his job. he can't raise a son his son is hot garbage, he has no real friends, he's not stupid but he's not particularly bright he's lazy.. you ever notice how he hears something and soon after he uses it even if the advice or phrase or quote doesn't fit... it's a running joke on the show.
Tony is what Rollo would call a Contextual Alpha
http://rationalmale.wordpress.com/2012/03/05/the-contextual-alpha/
When he meets a woman that has high self esteem he becomes a child. The woman from Italy (who was smoking hot), his therapist, the woman with the one leg who he ****ed and told him that she coudlnt' do it with him anymore beucase he was too sad all the time
there is only one real DJ / Alpha male on the show and that's Chris Motolsonti. Chris would be a real life DJ dude has just about perfect game / frame. I Mean lose the drugs or what not but even after aide he has NO problems finding good looking women and getting them to fall for him.