If someone makes the same spelling mistake repeatedly, it's not a typo, and IMO it's better to point it out, because they're probably carrying it over into more professional contexts and it affects how they're perceived.

Obviously in a personal context you'd try and do something like that in private, not in a group, but that's not really an option here.

If I repeatedly misspell something, or repeatedly use a validly spelled word in place of a homonym, I want to know.