Kant, quickly, is attempting to answer a question more along the lines of: What sort of character is most meriting good regard. While we might be upbeat for the individuals who live well and effortlessly, Kantians will probably regard those for whom a decent life is not a simple one. Since Aristotle and Kant are not attempting to answer similar inquiries in giving their individual records of prudence, it is not clear that they are truly in struggle with each other, in any event in the way that was at first thought. Some knowledge can be picked up by asking (or attempting to solicit) them the other's question.
There remains a leftover, however extraordinary, contrast between them: Kant is a great deal more cynical than Aristotle is about the likelihood of people carrying on with an existence without variant slants. Kant, being a decent Protestant, conceives that human instinct makes this incomprehensible and abandons us with moderation as the most that we can seek