A few years ago, I worked for Cookie Creations. We used the drill for our cookies also. We made the containers up in advance....like once a week. We used plaster of Paris to hold the sticks in position. We had an arrangement of sticks for 2 to 12 cookies. The sticks were different lengths and positioned so you would be able to see all of the cookies.
When we were ready to make a bouquet up, we took two sheets of tissue paper and laid it over the top of all of the sticks. We then pushed the paper down to the bottom of all of the sticks and left the corners up around the base of the sticks.
We then took each decorated cookie, drilled the hole, squirted a bit of the icing in the hole, and stuck it on the stick, which was already anchored in the container.
When you are doing hundreds of cookies a day, this system works great.
I have the icing recipe we used, which I have broken down, in size, for my own personal use. I love it because it tastes good, gets solid enough to stack the cookies, yet does not dry hard. I have a pic of some cookies I did for my grandson using this icing. I will add a link to it. We did most of our fill in using a #2 or 3 decorating tip. This icing was made the consistency to use that way. You could use this to make your outline but would have to thin it for flood work.
Cutout Cookie Icing
3 egg whites, at room temp. (you can also use MP)
Whip 2 min., fast speed or until stiff.
1/2 tsp. almond extract
1 tsp. vanilla
1 lb. powdered sugar
2 Tbs. Crisco
Mix on low speed until smooth.
(If you want to make a glaze from this, just add a little hot water.)