I make cookies one time a year - Christmas - but I make a LOT of them :)
These tips are so good I am sharing with everyone - and they make the whole cookie thing so much easier!
1) dough - for sugar cookies you can use a box mix or even the tubes of ready made, but add a little more flour to give them the heft to stand up to a cookie cutter.
2) when rolling out sugar cookies do not flour your rolling pin and surface, use powdered sugar to keep them from getting too tough,
3)(MY FAV)FROSTING - you want frosting like from a bakery - buy canned cake frosting and melt it in the microwave! (I use a white frosting and add food coloring for the colors I want) When you get it to a warm liquid (you may have to experiment, it doesn't take long as you can guess) you POUR it onto the cookies (you can use knife of back of a spoon to push it out to the edges but don't fuss with it too much, it begins to set quickly and the effect will be ruined) It dries glossy and gorgeous and if you make a fairly thick cookie and frost generously they will hold up all season long.