If you struggle financially I'm not sure I would consider New York. It is really expensive to live there. You mentioned you have family you depend on financially, do they all live in MI? Possibly you could go where they are if not.
I'm in PA. We do get cold weather but oddly enough our winters have not been so bad. I also am a person who suffers in the cold. Also in extreme heat. I often say maybe I should move but my whole family is here.
Good Luck with whatever decision you make.