I had a lot of pain the first couple of days, but it decreased quickly and was more like discomfort after the first week. The only time I had pain dilating was trying to cram a larger size dilator in without warming everything up with the one I was used to. As with everything else, YMMV.
Regarding the missing parts - actually, just rearranged parts - the only thing I miss is the lack of worry about urinary infection. A vagina and short urethra require more care than outside plumbing does, but everything in life is a trade-off and this is one I have been happy to make.
As far as expectations go, I believe that you shouldn't think that having a vagina (and being rid of the boy bits) will solve all your problems. It may make you feel better, physically and psychologically, but you will still be you and the world will still be the world.
I found a few dips as the exciting and energizing time of transition ended. Now I just have to live as Kate. I am anatomically, legally, psychologically, and socially female. Now what? Almost four months post-op, I don't hurt or ache anywhere, but I still don't have the energy I had before surgery. However, once my full energy returns, one plan for the "now what?" is to be on the prowl for some cute guy (or several).

- Kate