Yeah, Tony strangled Febby while dropping Meadow off at college. Yeah, he ran over Mahaffey in broad daylight. All violent, all criminal, but in the words of Paulie, "the game is the game". Not exactly flag-saluting types. However, the real red flag was when Tony gave Meadow the car that had belonged to Eric Scatino. That's when the sociopathy really shows.
At best, this shows a total lack of empathy and understanding of the human condition. Tony didn't even consider how Meadow might be perceived driving around in her friend's car while attending school with said friend. He thought she would genuinely be happy to receive a gift, even being her friend's car, especially considering he didn't even come up with a lie to say how he got it ("something like that""
At worst (and this is where I land), it was completely intentional. It was his version of the Johnny Boy Satriale moment: justifying violence and exploitation to numb his daughter to his way of living. It was a way to get Meadow's hands dirty in a public fashion. It was a way of saying, 'You don't like how I do things?' Well, you sure don't mind the perks."
When she pushes back and rejects the car, he flips. He launches into that moral tirade: how Davey brought it on himself, how people shouldn't make bets they can't pay, how she's on her moral high horse. He even talks about how he would sell the car to buy more stuff for the family as a reminder, and his "work" pays for their lifestyle. The car wasn't a gift but a direct statement to Meadow that "you benefit from this life whether you like it or not."
Up until this moment, Tony had tried to keep family and business as separate as possible (which was hard, considering season 1 was all about feuding with family), but in this moment, it slipped away. He gave his daughter something that would directly implicate her in his criminal activity in a public manner. In Tony's eyes, accepting the car would be accepting of him and all that he does.