Congratulations to have the courage to start. You do have some tough hurdles but it is not hopeless or impossible.
1. Yes. You need to see a doctor and a doctor who specializes in weight issues. You need to rule out medical causes unrelated to diet that can cause weight gain. They will be looking for conditions that affect you metabolic rate. Most of those tests can be done by taking blood.
2. You may be able to lose weight without surgery. But if that surgery is life saving don't discount it. You will only be recommended for surgery after a long evaluation period by health professionals.
3. Since you are young if you lose weight gradually you make not have a lot of problems with sagging skin. However, it may be that you will have folds after weight lost. That can be corrected thru cosmetic surgery. It is your health that is of first concern. Lose the weight. Tackle the cosmetic part latter.
I know your family history is discouraging. But you can change destiny. Start with small steps. Look at your habits and try some small changes where you can succeed. Build on these successes. Good luck.