Wash and prepare the bell peppers and tomatoes. Cut the bell peppers along the tops (as close to the top as you can) so that you have a bottom and a lid. Remove and discard the seeds and filling from the peppers. For the tomatoes, cut along the top of the tomato to create a lid or a cap. But don't slice all the way through, instead, leave a little bit of the lid attached to the tomato. Use a knife to cut around the perimeter and a spoon to scoop out the inside of the tomatoes. You'll need to keep the flesh of the tomatoes because we're going to add it to the gemista filling. Once you've scooped out all of the tomato fillings, use your hands or a fork to squish the tomato filling into smaller pieces. Reserve about 1/4 cup of this tomato filling because we'll be adding it to the bottom of the bell peppers later in this recipe. Place the tomatoes and peppers upright in your baking dish.
Roast the pine nuts. Preheat your oven to 200°F on bake. Spread the pine nuts on an oven-safe pan and place the pan in the preheated oven. Allow the pine nuts to bake for about 15 minutes or until lightly toasted. Then remove them from the oven and set them aside.
Make the gemista filling. Heat up 3/4 cup of olive oil in a large pot. Once the oil is hot, add two cups of diced onion. Sauté the onions on medium-low heat until the onions are translucent (about 10-15 minutes). Then add in the diced garlic. Continue to cook the onions with garlic until the garlic becomes fragrant (about 5 minutes). Then add in all of the ground beef. Use a large fork to break up the ground beef into small pieces. Continue to sauté the onions, garlic, and ground beef on medium-low heat for 20 minutes. Then, add in the salt, seasoning salt, sugar, Italian seasoning, black pepper, Greek all-purpose seasoning, and dry oregano. Mix together. Add in the tomato filling (from the scooped-out tomatoes) and allow the ingredients to simmer together for 10-15 minutes. After 10-15 minutes, add in the chopped mint, fresh parsley, fresh basil, and roasted pine nuts. Continue to simmer for another 10 minutes on low heat. Finally, add in the rice and stir together for a few minutes and then turn off the element and set aside. The rice in the filling will still be crunchy, but it will cook inside the gemista in the oven.
Cut and season the potatoes. Peel the potatoes, slice them in half and then in half again lengthwise to get four pieces per potato. In a medium-sized bowl, combine the potato wedges, 1/4 cup olive oil, 1/4 teaspoon Italian seasoning, 1/4 teaspoon garlic powder, and 1/4 teaspoon salt. Mix together so that the potatoes are well coated and set aside.
Assemble the gemista. Add about 1 tablespoon of tomato juice (from the reserved amount of tomato flesh earlier) to the inside of each pepper and sprinkle a pinch of salt inside each pepper. Sprinkle a little salt and sugar inside each tomato. You won't need to add any tomato juice to the inside of the tomatoes since they will release their own juices as they bake in the oven. Scoop the gemista filling from the pot into the tomatoes and peppers. Lightly press the filling into the tomatoes and peppers and spread it evenly inside. Place the lids back on the peppers and the tomatoes.
Bake the gemista. Add the seasoned potatoes to the pan and any extra liquid from the bottom of the bowl. Pour the can of plum tomatoes (and the juice) into a separate bowl and use your hands or a fork to squish the tomatoes together to make a sauce. Add 1/2 cup of olive oil and 1/4 teaspoon of sugar to the crushed tomatoes and mix them together. Pour the tomato sauce over the stuffed tomatoes, peppers, and potatoes and into the baking dish. Sprinkle the tops of the tomatoes and the tops of the peppers with breadcrumbs and grated parmesan cheese. Bake the gemista uncovered in the oven at 350° F on convection bake and on the second to lowest rack in your oven for about an hour and a half. The tomatoes and peppers will be soft and slightly wrinkly when they're done!