Cut the guanciale into strips and grate the pecorino cheese.
If using fresh tomatoes, bring a medium pot of water to a boil, add the tomatoes, and blanch for less than a minute. Drain and peel the tomatoes (the skin will come off easily).
Heat a teaspoon of olive oil in a large skillet, add the chili and guanciale, and cook until the guanciale becomes crispy.
Optional: Add the white wine and vinegar mixture, cooking over low heat until the alcohol evaporates (you’ll know when the alcohol smell is gone).
Remove the chili and a few tablespoons of guanciale. Set the guanciale aside and discard the chili.
Add the tomatoes and cook for 10 minutes, adding a few tablespoons of water if necessary.
Cook the bucatini pasta al dente, drain, and toss it in the skillet with the sauce, adding about 3/4 of the grated pecorino. Sauté for a minute.
Serve hot, sprinkled with the remaining pecorino and the reserved crispy guanciale.