BMI is a very old standard though and on its own is incredibly inaccurate. Here is a personal example. About two years ago I was around 160 or so pounds at 5'7" with around 6% body fat. According to BMI, I was at the bottom of overweight. Fast forward a little and I am still 5'7" but weigh between 145 and 150 with probably closer to 10% body fat. When I was at the bottom of the "overweight" part I could run ten miles and ask what was next. Now I am lucky if I could make three. BMI does not take into account your body fat percentage, your muscle mass, or how well your metabolism performs. If you are used to drinking cokes and eating doughnuts, your metabolism will perform quite differently than someone who is on a lean meats, nuts, and veggies type diet. Another measurement that BMI does not take into consideration is hydration. Most people, sadly, walk around dehydrated.The health advice you get on this forum is worth exactly what you pay for it.
OTOH, the experiences related are real.
Take your heights and weights and calculate your Body Mass Index.
The National Heart, Lung and Blood Institute has a BMI calculator here: http://www.nhlbi.nih.gov/guidelines/obesity/BMI/bmicalc.htm
Note the caveats they list. BMI is meant as a screening aid, not a diagnosic.
I suspect the notion that 400lb at 5' 7" is in good shape is a typo as the BMI for that is 63, or grossly obese
The OP says he is 5' 6" and 276lb, which works out to a BMI of 44.5. For that height/wt, obesity starts at 186lb and overweight at 155.
The person who is 6' 3" and 350 has roughly the same BMI, 43.7. Overweight for him starts at 200lb.
The formula I use is: BMI = weight in pounds x 703/height in inches squared. I can use that to calculate weight for a given BMI and height, which is convenient.
Full disclosure: I have been right around a BMI of 30 for a while.
The literature says a BMI over 30 puts one at much higher health risk for a number of things starting with heart disease, hypertension, and type II diabetes for starters. It also greatly increases the risk for some cancers. My suggestion is to first get a thorough health checkup from a competent physician and go from there. There are many NPs that are good in the field.
I am 73yo and wish I didn't have the "It isn't gonna happen to me" syndrome back when I could do something about it. I've been going to a gym, free thanks to Medicare, for about a month and am seeing the pounds come off a little at a time, but fairly steadily. I have pulmonary problems and the exercise helps with it, too.
IMHO, if you don't do the weight loss/conditioning under medical supervision, you are asking for trouble.
A BMI is a good start, but going and talking to a personal trainer or even a specialized doctor is a much better option in my opinion. Also, I would HIGHLY recommend subscribing to the Men's Health Magazine.