<p>I too have mixed feelings about this case. I think that based on your family’s finances, you might be better served by taking a 5th year at a prep school, and showing this continued upward trend in your grades. This might also give yourself more time to get healthy before beginning college. But I am confident that “repeating” a year of high school would somehow not go unnoticed. And then you would have to explain why you are repeating the year (when many kids get poor grades). On the other hand, you could take a 5th year and few colleges would question it.</p>