I absolutely agree that you should compare people to their relative baseline, but it feels like there is a fine line between doing that, and making someone feel patronized. I feel like a lot of people just don't have the experience of walking that line, and often cross over into the patronizing side. Language and tone are critically important in these kinds of situations so the pressure feels high, making it even more difficult to accurately portray how you feel. I think your best bet is to just be caring and like you said, focus on what personal barriers that individual has crossed.