Preheat oven to 325°F. Line 2 large sheet pans with foil and spray with olive oil.
Arrange bell pepper and onion halves on sheet pan, cut side down.
Squeeze juice and seeds from tomato into a small saucepan. Then place tomato halves cut side down on foil-lined pan. I used approximately 3 lb of tomatoes, but you want enough to fill 2 sheet pans with some space in between them. Using smaller, vine-ripened tomatoes will make your soup more flavorful. Add garlic cloves and thyme sprigs among the vegetables.
Drizzle olive oil over vegetables and sprinkle with salt and pepper.
Roast at 325°F for 60-90 minutes or until juices on sheet pan begin to carmelize and tomatoe skins begin to brown on top. While vegetables are roasting, simmer the tomato juice on very low heat. Watch carefully so it doesn't burn. Remove from heat if juice has reduced by a third or more.
Remove vegetables from oven. Discard thyme sprigs. Add roasted vegetables and cooked tomato juice to blender. Blend on high until soup has reached a very smooth consistency. Add in sour cream and milk and blend until combined. Taste the soup and add salt, pepper, and honey if desired. Soup may be hot enough at this point. If not, pour into a pot and heat on the stove until it starts bubbling.
While vegetables are roasting, prepare grilled cheese. Spread melted butter onto bread slices using a pastry brush. Divide cheese evenly among bottom slices of bread. Top with another slice of bread.
Arrange sandwiches onto cold griddle. Turn heat onto medium. Allow sandwiches to heat up with the pan. This ensures the cheese melts before the sandwich gets too done on the outside. Use a sheet pan to press sandwiches or use a panini press.
Cook for 10-15 minutes or until bottom side is golden brown before flipping. Cook an additional 5-10 minutes or until other side is golden brown.
Divide soup among 6 bowls and top with parmesan cheese. Serve sandwiches alongside soup. Enjoy!
To Freeze:
Add cooled soup to quart-size zippered bag. Freeze flat on a sheet pan. Can be stored frozen up to 6 months.