In a large saucepan, heat 2 tsp olive oil over medium-high heat. When hot, add onion and cook until browned, approximately 3 to 5 minutes. Add basil, oregano, garlic powder, salt, pepper, red pepper flakes, Pomi chopped tomatoes, Pomi strained tomatoes and chicken broth. Bring to a boil, then reduce to a simmer over medium-low heat. Simmer for 20 minutes.
Remove from heat and add to a blender. Puree until smooth. Add heavy cream and combine on low. Keep warm.
In a medium bowl, whisk together flour, cornmeal, baking powder, sugar and salt for the cornbread waffles. Add milk, vegetable oil and eggs, stirring until smooth.
Grease a waffle iron with cooking spray. Add 1/2 cup to 3/4 cup to your waffle iron, cooking until golden brown and cooked through. Once you’ve created at least 4 waffles, make the grilled cheese!
Add 1/2 cup of each type of cheese between two cornbread waffles to create a sandwich. Cook in an oiled skillet over medium-high heat until golden brown and the cheese is melted, approximately 2 to 3 minutes per side. Cut into quarters. Repeat with the second set of waffles.
Serve one bowl of soup with two quarters of each cornbread grilled cheese. Garnish with fresh chopped basil as desired.