steve, I can more than relate to your post and having been on both sides of the weight issue at some points in my life I can say for myself I think it has less to do with how much I actually weight and more to do with the lack of hope that I feel as time goes on. I'm similar to you - I have obsessed with working out, eating low calorie to literally see the scale go up. I can literally eat low cal, walk/even got up to running at some point and still nothing budged on the scale.
It's just the "hope" factor that you know no matter how hard you try you will struggle with each 1/4 of a pound that you lose and it's such an uphill battle that I've always just reverted to my previous way of life.
I'm sure with Oprah "accepting" her weight. I probably could too if I had the luxuries that she does. She has beautifully tailored clothes, hair and makeup done beautifully everyday, a stylist, and other wonderful perks and benefits to increase her "feelings" about herself that many of us regular people just can't afford. It always feel better no matter what weight we are at to wear a nice suit that fits our body well and in turn I'm sure it changes the way we view ourselves.
You can see this with brides - even plus size brides feel beautiful on their wedding days and probably feel an added sense of confidence knowing that even though they are large they still CAN be beautiful.
for me deciding on lap band had to do with giving myself hope. I can force myself to exercise, try to restrict my diet, but I need the added tool to be able to have mind over matter when it comes to my weight. I want to know it's something I'll be able to live with and I know it will be there to get me over the humps of issues that have caused me weight loss failure in the past.