I'm not debating that at all. If he's happy he's happy. But chopping his job off doesn't make him a woman.You would understand if you saw the before and after (mind out of the gutter, you know what I mean). I used to kind of dread seeing him if it wasn't at a get together where he came out of his shell a bit wih a drink in his hand, we used to get on really well then.
I couldn't imagine being trapped in the wrong body for 30 odd years, it must be horrid. No one deserves to be painfully unhappy if there are options to correct it.