1 / When is a good time to schedule for Christmas photos?

As early as September.  My family usually does it in September.  I highly recommend doing it in October or November so you leave yourself plenty of time to work on your card.

2 / What should I wear at my photoshoot?

Even though I emphasize unpretentious photography, it does not mean there is no preparation involved.  In fact, a good photo shoot begins with careful coordination of choice of clothing.  A general rule of thumb is coordinate the same color scheme of clothing within family members.  For example, warm colors include red, orange, yellow.  Cool colors include blue, green, purple.  Any shade within the scheme will look good with a mix of some neutral colors.  No graphics, logos, or words on your top.  Solid colors are always popular but a mix of pattern such as checkers, stripes, polka dots, flowery prints... are fun ways to dress up the shoot.

3 / Do I have to hire someone to do my makeup?

Depends.  Depends on the theme of your photos.  If you want very formal photos with elegance, I recommend hiring someone.  If you are going to the beach wanting some causal pictures, you can do your own makeup.  I highly highly highly recommend ladies wearing some make up.  A good foundation, heavier on the eyes, some blush, and lip color.  Some of my clients love false lashes and I never say no to that. Trust me, you will love the photos 100x more if you make yourself look healthy and bright!!