To prepare the tomatoes:

1. Quarter the tomatoes and spread them on a baking sheet.
2. Sprinkle with garlic powder, olive oil, salt, and pepper.
3. Bake at 200°F for 4 to 5 hours until softened but not browned.
4. Transfer to a container, add red wine vinegar, and refrigerate until cooled.

(You can make these up to one week ahead.)

To assemble souffles:

1. Preheat oven to 375°F.
2. Cut the puff pastry so each piece fits the diameter and height of your 5-inch souffle pans. Press the pastry into the dishes. 
3. Cook the bacon, drain and chop into ½-inch pieces. 
4. In a medium bowl, whisk the eggs and milk. Add all cheeses and stir to combine.
5. Divide the egg mixture evenly between the pastry-lined dishes. 
6. Sprinkle bacon on top. 
7. Cut the remaining puff pastry pieces into eight 2-inch by ½-inch strips. Place four on each souffle to form a decorative top.
8. Bake for 5 minutes. Remove from the oven, add roasted tomatoes to the top, and return to bake for another 10 minutes or until puffed and golden. 
9. Let cool for 5 minutes before serving.