Understanding what it's like to be (dis)privileged

Can a person privileged in some respect understand what it is like to be disprivileged in that respect? Some say yes; some say no. I argue that both positions are correct, because ‘understand what it is like to be disprivileged’ is ambiguous. Sometimes, it means grasp of the character of particular experiences of disprivileged people. Privileged people can achieve this. Sometimes, it means grasp of the general character shared by experiences of disprivileged people. Privileged people cannot achieve this. However, there is a general kind of understanding that they can achieve: understanding of why individual experiences have their character, in relation to privilege and disprivilege. This understanding is a skill, not knowledge. It is difficult and discomforting for the privileged to acquire and is easily conflated with knowledge of general experiential character. Distinguishing and characterizing these kinds of understanding clarifies whether, and how, the privileged might understand what it is like to be disprivileged.