Hi, paperwhite, and welcome to DC.
When my children were small, they are in their 30s now, baking cookies was always a fun activity, especially at Christmastime. Here's a recipe I use and have had for well over 30 years. It works perfectly for me every time. I use powdered sugar to "flour" my rolling surface because it keeps the cookies from being tough. The cookies are even easier to remove from the cookie sheet these days now that baking aids such as Silpat and Teflon baking liners are available.
Here's the recipe:
GLASS WINDOW COOKIES
¾ cup shortening (part butter or margarine)
1 cup granulated sugar
1 tsp. vanilla extract or ½ tsp.lemon extract
2½ cups all-purpose flour
1 tsp. baking powder
1 tsp. salt
6 pkg. hard roll-type candy, like LifeSavers in clear flavors (cherry, lime, lemon, orange, etc.)
Cream together shortening, butter or margarine and sugar. Add eggs and flavoring. Sift together flour, baking powder and salt. Blend into creamed mixture. Cover dough and chill for at least 1 hour.
Roll dough 1/8-inch thick on a cloth or board lightly dusted with powdered sugar. Cut into desired shapes using cookie cutters of two sizes to make cutouts, or make your own patterns using heavy paper (cutting around the pattern on the dough with a knife).
Place the cookies on an aluminum foil-lined or Silpat-lined cookie sheet. If you plan to make large cookies, cut out the “window” portions after
the cookie has been placed on the cookie sheet.
Fill the cutout windows with pieces of candy. Small windows will make it necessary for you to break the candy into smaller pieces. Fill the windows with candy until the candy is just level with the dough.
To make hanging the cookies easier, punch a hole ¼-inch from the top with a plastic drinking straw.
Bake the cookies in a preheated 375º oven for 7 to 9 minutes or until cookies are very light brown and candy has melted. If the candy has not spread out within the cutout design at the end of baking time, spread with a metal spatula immediately upon removing from oven. Cool completely before removing from cookie sheet.
Store cookies, separating layers with waxed paper, in an airtight container.