I have only made a few cookies - the shoes, hats and purses in my gallery. I was wondering if instead of outlining and then flooding cookies, if anyone lays the cookies on a wire rack and floods the cookie letting the icing run down and completely cover the sides. Would this work for certain types of decorations?

sure. I dip the faces of some of my cookies. It just depends on the look you want or need for the design. There are companies who use a paint brush to apply the background.

You don't even need to do that! If you thin your icing to just the right flooding consistency, you can flood to the edges of the cookie WITHOUT the icing dripping down the side.

I like to 'outline' with my flood consistency icing, then pipe a blob in the center and spread it to the edges with my piping tip. This ensures that I don't pipe too much icing close to the edge, causing it to drip over.

Here's an example:

http://www.cakecentral.com/modules.php?name=gallery&file=displayimage&pid=1127583

Thanks! Your cookies and cakes look great!

I outline and then immediately flood with the same icing, piping it on in a zig zag pattern. I then smooth the icing with an off-set spatula. I rarely have a problem with the icing dripping over the sides, and using the spatula eliminates the possibility of hidden air bubbles.