To make the chipotle bourbon dressing. In a small saucepan over medium heat, bring bourbon to a boil. Cook until liquid is reduced to about 2 tablespoons, 3 to 4 minutes. Transfer to a bowl and refrigerate until well chilled. Once chilled add the olive oil, vinegar, honey, chipotle pepper and garlic. Season with salt and pepper and whisk to combine. Set aside.
Preheat oven to 400 degrees F.
Line a baking sheet with foil. Arrange bacon strips about 1 1/2 inches apart. In a small bowl stir together brown sugar and cayenne pepper. Sprinkle the mixture evenly over bacon. Bake 14 to 16 minutes until bacon is browned and crisp. Transfer to paper towel; cool. Halve slices.
While the bacon cooks make the corn fritters. Add the flour, brown sugar, sugar, baking powder, salt, pepper and 3/4 cup of the corn to a food processor. Pulse until blended together, then transfer mixture to a mixing bowl. Stir in remaining corn and milk, mixing until a batter forms. It should be the consistency of a thick pancake batter.
Add oil to a large skillet saucepan and heat over medium high heat.
When the oil is hot add a little less than 1/4 cup of batter to the skillet and then quickly smooth the batter out to a circle. Cook for 2 to 3 minutes, flip and place one slice of gouda cheese right on top of the fritters (leave 4 fritters with no cheese). Cook another 2 minutes or until brown and crisped all over. Remove and repeat with the remaining batter until all the batter has been used. Keep the fritters warm.
To assemble, place four fritters with cheese on 4 plates. Spread with mashed avocado, arugula, tomatoes and a few slices of bacon. Top with another cheesy corn fitter and repeat the layering. Finally add the non-cheesy fritter (should be the 3rd fritter, 3rd layer) and top with a few arugula leaves, tomatoes and bacon. Drizzle with the chipotle bourbon dressing.
The stacks are really pretty, but if you want these to be an easy eat then just leave the fritters unstacked. If you do this though, I would make a little extra bacon and add another avocado. Unstacked fritters leave more room for toppings!