To Re-roll or Not to Re-roll & First Cookie Failure

I've baked my fair share of rolled and cut cookies.  I find myself often faced with trying to decided whether or not to keep rolling the dough to maximize my number of cookies, or just roll once and get only cookies with the best texture. 
I learned to bake primarily from my mother.  She used to bake us "breakfast cookies" when we were kids.  They were heavy and nutritious with whole wheat flour, oats, nuts, dried fruit, natural sweeteners, and for a little something special she'd toss in a few chocolate chips.  We were thrilled to get cookies for breakfast, and she could commend herself for fueling our days with more than could ever be found in PopTarts or a bowl of Cocoa Puffs.  When I started school, she went to work full-time.  I adored my mother (I still do), and could still spend an endless number of hours with her in the kitchen.  With her going to work came my opportunity to explore food.  She has always been wildly enthusiastic about our productive interests, and let me run with my desire to build my home base in front of the stove.  By the time I was 10, I was making dinner for our family, baking birthday cakes, and taking on new recipes, regardless of skill or tools required, with my "how hard can it be?" attitude - possibly my best and worst attribute.
While I was in culinary school, I worked for a semester with a pastry chef who had a long history of formal training, work in Paris, bakery and cafe ownership and was crazy in her passion for pastry.  Her enthusiasm and her expectation that the end result had to be perfect is something that I've tried to find a home for in my personality. 
Sometimes, the end result is far less than perfect.  My action plan for today consisted of 1942's Honey Refrigerator Cookies - a war-time ration-friendly recipe, 1972's Dutch Caramel Cashew Cookies, 1943's Scotch Oat Crunchies, and 2006's Chocolate Peppermint Bar Cookies.  The final cookie tonight was that first in about 20 varieties to fool me.  With a 1/2 cup of butter, flour, cocoa, 3/4 cup brown sugar, 1 egg, some leavener, salt, chocolate chips, and crushed peppermint candies, I was absolutely stumped at how I would get such a small quantity of batter into the 13X9 in. pan called for in the recipe.  I decided I would improvise and pull the foil lining up enough to prop one side up with a bread pan, making the baking area seem more reasonable.  I spread the batter in this space, popped them in the oven, and peeked 15 minutes later to find a liquefied, puffy, bubbling mess.  Did I crush the candies too finely?  Were they going to spread through the entire pan eventually?  I baked them until I guessed they would be as close to done as they might get, and am hoping that after they cool, I'll get a salvageable product.
I'm glad to have grown out of my teenage disdain for my mother's style of cookies, and just for the record, I gently re-roll my scraps once and then throw the remaining dough away.  I am, however, always open to learning something new.