Presentation is always important. You can turn the simplest and easiest thing into something beautiful with just a bit of styling. It doesn't have to be perfect - receiving handmade items are special, which is why I still write letters, hand make greeting cards, and package Christmas cookies every holiday season for family and friends.
Choose a vessel that is not labor intensive. Balance cost with attractiveness - if you know that you are baking for Christmas and it's October, start buying the packaging when you see a sale or find a coupon. I like using the small food-safe paper bags from Michael's as they have a firm shape, but are forgiving and malleable.
Prep
Bake and chocolate dip and decorate the night before you package. The biggest mistake is packaging warm items. Warm equals sticky, and sticky means that all you hard work is melding into a beast of a baked good. The person receiving it will want to eat one cookie at a time.
Bake an equal amount of everything, plus extras. There's nothing like getting halfway through packing only to realize that you've run out of one type of cookie.
Layout everything like the image below. Prep all the parchment to place in between the cookies, open up all the bags. Keep your area food-safe by doing all the touching of everything like scissors, etc. beforehand.
Packaging
Wash your hands. Wash them up to your elbows. Before you wash your hands, put your hair back (or wear a hat) and make sure that you have on a clean apron. You are giving food to other people and your reputation is on the line. Keep it clean!
Create an assembly line. The less you have to handle items, the less chocolaty smudges you'll leave on the pristine packing and the less cracked cookies you will have.
Have a buddy. My husband is the gopher - the one who can remove empty plates or cut more parchment - and helps me keep everything clean and organized. Don't have someone to help? That's okay - just plan ahead.
Personalize the bags. Write a fun message, and don't forget to write their name on the bag, even if all the bags are the same. It makes it feel less generic.
Figure out transportation - what are you going to carry these in? There's no sense in going through the process only to realize that there ins't a bag in which to carry.
Happy baking!
