Good luck to you, I hope you get approved soon. I am in the same boat, high cholesterol, high bp, plantar fasciitis, family history of diabetes and heart disease. About a year ago I had a BMI in the 30s (with all the same issues), but managed to "diet" my way up to BMI 40. I am paying for surgery since my insurance does not cover WLS at all.
I still fit in size 16/18s, which I guess some people consider "not that big", but my health issues demonstrate that it is WAY too big for me.
I live in the land of the ultra-fit, with every single one of my friends quite thin and in very good shape. Honestly, the only fat people you see in our town are tourists! So although I have less to lose than some, I am painfully aware of that weight every waking moment. I too have been dieting since I was 12, and although I could lose, I could never keep it off. This has gotten more and more difficult now that I have hit the 40s.
I am still planning my strategy for keeping what I consider a private medical concern private. I have told my DH, kids, and mom. That is it.