I think Tony is just impulsive and, like many convicts who’ve spent time in prison, emotionally immature/stunted. He said himself, he has problems with impulse-control. You can tell Tony’s been through some therapy or rehab program at some point, the way he talks about/explains himself - addictive personality, addiction to women, problems with impulse-control, etc.
I don’t know if he intends to move on soon because I don’t know how long he is on parole for. But until he gets off parole, he has to stay at Angela’s house because that’s the address he gave the parole officers. So. The true test of how genuine his feelings are will be once he gets off parole. The fact that he said, “It’s almost not worth it,” when Angela made the list of rules makes me think he’d be gone if he felt he had a choice in the matter.
IDK. Tony reminds me of an adolescent that is pissed off at his parents rules. I mean, it sucks, to be a grown adult and have to answer to someone else. I think he and Michael are similar in that way - they’re grown and want the freedom to engage in whatever wanton behavior and debauchery they please, but are constantly limited in doing so because they depend on women to support them and these women expect them to be faithful, so there’s a constant conflict between doing what they want to do and survival. In terms of supporting themselves, conning is what they know.
Mind you, Tony is not NEARLY as openly disrespectful as Michael is, but I think they are both users. I think Tony is just less blunt about his feelings (likely because he’s been through therapy or rehab and repeats what the counselors have told him) and explains away his behavior with psychobabble catch-phrases like “addiction to women,” etc. Michael comes from a different background, was convicted of very different crimes and is not an addict, so I highly doubt he’s been through any sort of therapy or rehab, so he explains his behavior and feelings in a much more blunt, cold and unapologetic manner.