Eat MORE calories??!! Help

I have been on MFP for about a year. I started because my dr. put me on a low dose of cholesterol medicine. My cholesterol was too high and so was my weight. I changed my diet, and cholesterol numbers came down after a month, but not enough. So doc put me on meds. My goal was to get off the meds! So I saw a nutritionist, she had me eat 1900 cals a day. I did this lost 10 pounds, Christmas came around, gained it back. Started over in January eating 1500 cals a day. Lost 10 - 12 pounds. Weight kept stalling. Now also, I exercise a good amount. On my breaks at work I walk, I do kickboxing with actual punching bags (my favorite class), hour long zumba classes at my gym, weight training, bike riding, whatever I can fit in. And I try to do this at least 3 days a week. Sometimes 6 days a week. To get over this 10 -12 pound slump I recently started jogging. (The hardest thing in my life) That got me down to 16 pounds. Saw the doc, going off the meds to see where cholesterol levels are. Now let me also say I am a 37 year old female originally weighing in at 281 pounds. I NEVER ATE BACK ANY EXERCISE CALORIES. I figured I have this much weight to lose, the bigger calorie deficit the better. My doc has encouraged me to eat back every single exercise calorie. She thinks I have made my metabolism go into starvation mode by doing such high calorie burning exercises and not eating enough calories. Now mind you, over this year I was not 100% consistent. Sometimes I would fall off the wagon, but learned to get back on. But I would say generally I tracked most days of the YEAR. And honestly KEEPING off those 15 pounds in a year is definitely an accomplishment. I used to always gain it back. But I am terrified of eating more food and gaining back those 15 pounds that took me a year to take off! Any constructive advice is very welcome. Anyone else in this same situation? Sorry for the book.