My best advice is practice, practice, practice! It really does get faster the more you do it, and if you put on the right stuff, you can have a stunning (yet subtle) look done in about 15 minutes.
I'm with Charlotte though... as soon as my hair removal is closer to done (I'm about halfway) I'll start phasing out the foundation and powder as much as possible. My own routine is liquid foundation, a tiny bit of cream blush (can't stress that word enough:
tiny), pressed powder, eyeshadow to darken/shape my eyebrows, eyeliner, mascara, and lipstick (the liquid variety). Takes about 15 minutes where it used to take nearly an hour when I first started. I'm wearing all of this in my avatar pic.
HRT hasn't made a dent in the copious amounts of oil my skin produces, and even though I use oil-control foundation and powder, I still need to wipe off my face and reapply after four or five hours (and that's on a cold, dry day even). You'd think, with how oily my face is, I'd be a poster child for acne, but I've always had an extremely clear complexion even through years where I never washed my face outside of my morning shower. A lot of people will tell you moisturizers are also an essential part of your daily makeup/skin-care routine, but moisturizer only makes my situation worse and so I save my money.

The only time I tend to break out is when I use moisturizer or sunscreen.