I hear you with the short hair thing! My hair's the longest it's been in ages, and it's not even hit the base of my neck yet. I put a good whack of hairspray in before putting on the wig cap, holds everything in place and also gives the bobby pins something to hold on to when you're pinning the wig into place.
I don't have much in the way of a suggestion for make up, I'm pretty basic myself. But more around the eyes makes a huge difference when it comes to photos. There are some awesome tutorials on YouTube for enhancing features. I'd link you to some favourites, but with my net the way it is right now, using YouTube is like trying to walk on the ceiling.