By far, unfortunately, is no. I spent the whole Winter doing Volunteer work, drinking Courage coffee, watching HMovie, and also chose to have more courage at the end of Year 2 (to unlock speaking to Howl in the forest), however, my Courage stage was still at Heroic. I can't unlock the Howl scene in the forest (not his love path), so if you guys somehow have the same problems or I did something wrong, please let me know. Tysm!