I think you are using empathy with your dad, you know him well enough to know what he does and doesn’t like, and you don’t do what he doesn’t like because you understand, and you don’t want to negatively affect him. I think empathizing is easier when you know someone. It doesn’t have to be what you would do, that’s just a helpful mindeset when you’re trying to empathize with strangers. The problem with words that need to be applied on an individual level is they need to be applied on an individual level. That means empathy is unique to every situation, which makes it difficult to pin point an exact definition.

I think the mistake people make is assuming empathy can be used in a general sense. You brought up homelessness, and obviously it’s easy to say “I don’t want to be homeless, so homelessness is evil”. That isn’t empathy though, it’s just an opinion based on the sympathetic feelings caused by others circumstances. Empathy is considering beyond feelings, and considering the actions you would take in someone else’s circumstance. Then weigh your thoughts against the actions of those you’re trying to empathize with. Empathy is useful in individual cases, not generalizations. You know the framework of someone’s story, and you use assumptions and imagination to fill in the blanks. Too often people assume empathy means you must be kind to someone, when it could just as easily make you realize how wrong someone is when you know their side. The word (like many others) is almost relegated to nothing more than a political tool at this point. Definiations can change from party to party, or generation to generation. I’m sure people will disagree with my take on the word.