Very nice try, wolf, but you fail. It's a common mistake -- you took the objective approach, and this conversation is about the subjective approach.
Y'see, the actions of these people are irrelevent, because there is no knowable objective reality. Instead, every living person creates their own subjective reality. In order to communicate with another person, your subjective realities must have something in common (hence the value of empathy). You cannot communicate with another person without being transformed.
One way to get into this mindset is to contemplate the question: "
How long is the Emperor's nose?". Since it is impossible to measure the length of his nose, what you think is the length of his nose is pure guesswork. However, if you could compare your guesswork with the guesswork of everyone else in the country, you could get a precise value for the length of his nose.
Likewise, since objective reality is fundamentally unknowable, the best way to learn about it is by comparing your subjectivity with someone else's. The smaller the difference between your subjectivity and the other person's, the easier it is to communicate. The greater the difference, the more you can learn from them. Fox News uses this method to search for the truth.
It is important to remember that "one subjectivity is not inherently superior to another", because, after all, it's subjective. Therein lies the beauty of the subjective approach: because every subjectivity is valid, we are freed from the chains of judgement.
Now let's try to answer these questions the subjective way.
1) The drug-crazed sociopath who beats, rapes and kills your sister.
The sociopath knows much more about pain and neglect than you do. The sociopath occupies a more visceral subjectivity, one full of contrasting colors, vividity and darkness.
2) The crooked CFO who loots his company's pension fund, leaving elderly people penniless while he buys a mansion, a boat, and new boobs for his girlfriend who replaced his wife of 25 years.
The CFO occupies a much more placid subjectivity than the sociopath, and is probably less painful to talk to (unless you retch when you learn why he ditched his wife and looted his company). The CFO obviously worked hard to get to his position. It would probably be very pleasant, in fact, to talk with the CFO on his yacht while smoking his Cuban cigars.
3) The punk who smashes out your @250.00 car window to steal your $15.00 CD laying on the front seat.
Fortunately, you have an obvious commonality with the punk: similar taste in music. Music gives order to subjectivities, so it is sure that you will be able to communicate with the punk on a large number of issues. Since the punk was willing to smash your $250.00 car window, he is clearly a free spirit. His subjectivity is probably untainted by social mores or book learning and therefore more pure. Be glad that you were able to meet the punk: $265.00 is a small price to pay for the value of this meeting of the minds.