Will I gain weight if I increase my daily calories by 100/day every week? I want to get to healthy maintenance levels.

Diet and muscle mass. To gain weight you have to consume more calories than you are burning. Do this in a healthy way though. Don't choose junk or fast food. Keep a well balanced diet and make sure you are getting all the nutrients you need. Don't cut out exercise as it is very good for you. Weight lifting and other muscle building exercises can help you increase your body mass.