Wait, is that actually culture-specific, or are tricksters typically sympathetic?

I'm not sure "sympathetic" is the right word. I'm not an anthropologist, but the impression I get from reading trickster stories -- whether we're talking about Raven or Anansi or Reynard the Fox or Gregory House -- is that the main appeal comes from watching the protagonist do things to annoying people or institutions that would get you fired or incarcerated or at least get your ass kicked, do them with style and without remorse, and get away with them at least for a time. It's a schadenfreude thing, and it's fun to watch even if the character is depicted as an unrepentant jerk -- which most of them are.