Is the real distinction you are drawing between someone who knowingly does wrong and then manages the consequences, versus someone whose harmful behaviour comes mainly from foolishness or immaturity?
If so, I would think deliberate maliciousness is the more serious moral problem. Foolishness can certainly cause great harm, but knowingly exploiting or hurting someone is a different thing altogether. And if the “repentance” is only meant to contain the consequences, I am not sure I would call that repentance in the first place.
Hence, I suspect your question is rhetorical rather than a request for a simple ranking.
The Quran seems to make an important distinction between wrongdoing committed in jahālah foolishness/recklessness followed by genuine repentance (4:17), and a person who knowingly persists in what he is doing:
وَلَمْ يُصِرُّوا عَلَىٰ مَا فَعَلُوا وَهُمْ يَعْلَمُونَ
“…and they do not persist in what they have done while knowing.” (3:135)
So if one person is genuinely foolish and immature, while the other knowingly acts with malice and then merely does enough to contain the consequences, I would find the latter morally more troubling from a Quranic perspective.
In fact, I am not sure that damage-control after deliberate malice is what the Quran means by tawbah at all. Tawbah implies turning away from the wrong, not simply neutralizing its consequences.