Wash tomatoes. Cut the medium vine-ripened tomatoes in half (horizontally). Leave the cocktail tomatoes and cherry tomatoes whole.
Put half of the oil in one pan over a medium to high flame on the stove. Put the other half of oil in another pan also over a medium to high flame.
In one pan place the medium tomatoes open-side up. In the other pan place the whole cocktail tomatoes and cherry tomatoes. Add some salt and black pepper. If you are adding herbs, add them in at this time if dried or before placing the dish in the oven if fresh herbs are used. Leave to cook about 5 minutes. (The smaller tomatoes may need less time).
When the tomatoes have darkened on the bottom, add half the balsamic vinegar and sprinkle half the sugar into one pan and the other half of balsamic vinegar and sugar in the other pan. Careful not to put them on the tomatoes, but into the pans. Tilt the pans to mix. Reduce heat and continue to cook uncovered about 20 minutes, turning over the tomatoes gently from time to time.
The tomatoes should remain in tact (whole) and the liquid in the pan should become thicker like a syrup. Turn off the flame.
Place the tomatoes (the open-side up) in a baking dish in an attractive pattern. You can add some of the remaining syrup in the bottom of the dish, but don't add much as the pie won't caramelize well if you put in too much syrup.
If you are adding toppings, such as cheese, spread the topping on top of the open-faced tomatoes.
Roll out the puff pastry dough and place loosely on top of the pie dish, folding the edges into the pan. Don't prepare the crust borders like you would an ordinary pie as you will turn the dish over onto the crust when it's cooked, so the crust needs to slide out.
Place the pie dish in the middle of a 200°C / 400°F preheated oven. Bake for about 20 minutes or more until the top is lightly brown.
Remove the dish from the oven and let cool about 10 minutes before turning it over onto a plate. I use another baking dish of the same size to turn it over into.
Slice it into the portions desired. Serve and enjoy!