Start the pasta water.
Arrange the chopped sausage, cherry tomatoes, pepper, onion, and cherry tomatoes on an oiled cookie sheet and roast for 30 minutes on 400F, stirring everything up every 5 minutes to evenly brown.
In a skillet, place the whole tomatoes, 2 handfuls of small tomatoes, cherry size works too. Add the grated garlic and add 1/8 cup of olive oil and salt, cayenne, and pepper. Stew them for about 10 to 20 minutes until it's a mash. Press on the tomatoes with a masher or fork to get them into a stew. Shut the heat off, add the herbs and then cover the pan and let it sit.
When the pasta is just before al dente, strain it and add it to the skillet with the stewed tomatoes and mix it up, cover it, put the heat on low, and let it sit for 2 minutes. Add the roasted sausage and peppers and mix, then add the rest of the 1/8 olive oil, or more if desired. Check the salt, pepper, and chili level (you may want more), and toss. Sprinkle the rest of the herbs on top.