Preheat oven to 325°F with a rack in the center.
Place butter and sugar in a large bowl (or the bowl of a stand mixer).
Beat on medium speed until lightened in color and fluffy.
Add the vanilla extract and beat to incorporate.
Add the flour and stir in gently with a spatula or wooden spoon until incorporated. You may want to mix the last bit with your hands. Don't overmix, or the cookies will be less tender.
Divide dough in half and shape into two discs.
Dust work surface and rolling pin with flour and gently roll each piece of dough into a ¼-inch thick circle(-ish).
Cut into 2 ½-inch rounds (or really any shape you like) using a cookie or biscuit cutter. You can re-roll any scraps and use them to make a few more cookies.
Transfer cookies to cookie sheets lined with parchment and chill in the fridge for 15 minutes to help cookies retain their shape in the oven.
Bake for about 15 minutes, until cooked through. You can look for light browning around the edges, though cookies this thick sometimes stay pale when baked.
Remove cookies from the oven and transfer to a wire rack to cool.
When cookies have cooled completely, make the caramel layer by melting the unwrapped caramels and the cream in a large bowl in the microwave. Watch carefully, since it will begin to bubble up shortly after it's completely melted.
When caramel is melted, place about a tablespoon (depending on cookie size) in the center of each cookie and spread with the back of a spoon. Let caramel set before proceeding.
For the chocolate layer, melt the chocolate chips and coconut oil together in short bursts in the microwave, stirring between bursts.
Spread about a tablespoon of chocolate onto each cookie and spread it with the back of a spoon.
If using eyes, position them while the chocolate is still hot.