There is generally held to be a deceitful and manipulative element to cunning but being considerate requires exactly the same mental processes, only for nicer ends. You hear a lot about low cunning but very little about high cunning. That's because high cunning is perpetrated by people so above suspicion that you don't even notice it. Flattery is sugared cunning.
Cunning people and animals are generally portrayed as thin. Aesop doesn't have many fables about the cunning hippo. This has advantages for the larger person as no one suspects them of being crafty. The fox has a reputation for cunning but is actually not very bright. It just makes people who hunt feel better to claim they're after a four-legged Houdini. For the same reason, fishermen often complain that fish are a bit slippery.
There are no evening classes in cunning. Lessons in cunning are learned the hard way. Crafty people aren't smarter than other people; they've just made more mistakes more often and can now avoid them. Young people are rarely cunning because they're still crashing through the pre-cunning disasters.
The cunning tend to assume others are also cunning, and they start getting so clever and sly and devious, they end up making bigger fools of themselves than those entirely without guile. Their one weakness is they think their cunning is invisible. It's not, especially if you're not very good at it. Then people regard you as if you were wearing a silly hat: if you want to look ridiculous, that's your business.
In the past, Cunning Folk were the wise men and women of rural communities who claimed to be able to help in affairs of the heart, health matters and witchcraft. They were much like modern-day therapists in that their main skill was being able to lead people into thinking about their own problems at a much more complex level than the initial problem warranted.