In a large mixing bowl combine: the flour, 2 tbsp brown sugar, baking powder, baking soda, and salt. Mix well.
Melt the butter in the microwave and allow a few minutes to cool.
Measure out 1 cup of milk into a measuring cup with space to add 1 cracked egg. Mix well to combine. Once the butter has cooled a bit, add it as well.
Make a well in the center of the dried ingredients and pour in the wet ingredients.
Mix it all together until it is just combined and there is no dry flour. Don't worry about it being lumpy, the lumps will cook out. You don't want to overmix the batter.
Once the waffle maker is hot. Brush butter on both top and bottom of the waffle maker then add your batter. Cook until brown.
While the waffles are cooking, put the 1/4 cup of milk. 8 tbsp of butter, and brown sugar in a medium saucepan. Stir to combine. Set over medium high heat. You just need to bring the syrup to a simmer. Once you have done that and the butter is fully melted. Remove from heat. Syrup will slowly start to thicken but should stay pourable for at least 20 minutes or so before the butter hardens too much.
Finish cook the waffles and serve immediately.