The addiction begins with the vision for a beautifully crafted cookie and one stinkin adorable cookie cutter. That works out so well, you pick up five more because they are on sale at Michaels's. Then Amazon runs a set of 100 on the Deal of the Day and the next thing you know, you have enough cookie cutters to fill a bathtub. Some are metal, some are plastic and some are custom made with filament from a 3D printer. You have some that are your obvious favorites, either because they make such a clean cut or they are easy to use or make such an adorable cookie. Then there are those that make you say ugly words.
The most frustrating cookie cutter is usually one that has small appendages where dough likes to get stuck. I am thinking specifically about the middle bar of the Georgia G, Olaf's little twigs on his head, the top knob on the teapot etc. I have suggested to people before that if you have a cookie cutter that likes to tear up the dough when cutting, only "score" the dough in the tight places. Freeze for about thirty minutes then you can whip around the score marks with a paring knife. It is much faster than trying to negotiate with soft dough.
Before I purchase a cookie cutter, I evaluate whether or not it is going to be difficult cooperating. Take the innocent looking shamrock, for example. A shamrock has a skinny little stem but if you don't break it getting the dough out of the cutter, you most likely will break it getting the baked cookie off the stone. If it survives both of those it will surely break once the stem gets softened by the frosting and you put it in a box. The same goes for the little pom pom on Santa's hat and the skinny stem of the martini glass. If you are designing a custom cutter, make skinny little appendages more sturdy by drawing a wider channel. You can always give the cookie the illusion of the tall thin martini stem with a thin stream of frosting. And if the cutter is the least bit bendable, I will bend that pom pom on Santa's hat close to the face so that when baked, it will fuse itself to the side of his face and become a strong cookie. If that pom pom snaps off, that expensive cookie is no longer sellable.
Most commercially produced cutters are fairly sturdy designs because they already know people won't like a cutter where dough gets stuck. However, you will run into this problem frequently with custom cutters where the printer will print any design you can draw, whether or not it will yield a good cookie. Remember the size 24 bikini. Just because it can be made, doesn't mean it should!