Chili: Place a large pot over medium-high heat. Add oil to pot, followed by onion, poblano and jalapeno and saute for 3 to 4 minutes. Add butternut squash and continue to saute for an additional 3 to 4 minutes. Season with salt and pepper.
Add cauliflower, garlic, chives, oregano, and bay leaf and stir together. Add chile powder, paprika and cumin and continue to saute mixture for 4 to 5 minutes.
Stir in diced tomato with juices and lower heat to medium. Season with salt and pepper. Simmer mixture for about 15 minutes, adding ¼ cup of broth at a time, if mixture gets too dry.
Stir beans into chili and simmer for 5 minutes. Remove from heat and pour into a 3 quart baking dish. Set aside. Vegetables should be tender with a slight bite to them (they will continue to soften in the oven).
Preheat oven to 400˚F.
Place flour, cornmeal, baking powder, baking soda, sugar, salt, and pepper into a large mixing bowl and whisk together.
Cut in butter with a pastry knife or using your fingers until a fine grainy texture forms.
Fold buttermilk into mixture until a loose dough forms.
Scoop ⅓ cup sized dollops of biscuits all over the top of the chili, until fully covered leaving about ½ inch space between each biscuit. Brush tops of each biscuit with melted butter.
Bake cobbler for 15 to 20 minutes or until biscuits are golden brown and vegetables in chili are fork tender. Cool for 10 to 15 minutes before serving.