For the vegetables: Preheat the oven to 400 F. Place the tomatoes, onion and garlic on baking sheet. Drizzle lightly with olive oil and roast until the skins are blistered and the vegetables softened, about 40 minutes. Remove from the oven to cool. Once cooled peel the garlic.
For the mole: In a large heavy saute pan heat ½ cup olive oil. Fry all chiles in one batch for about 40 seconds, turning constantly, until fragrant. Transfer to paper towels to drain. Meanwhile heat 4 cups vegetable broth. When boiling, add chiles, reduce heat and simmer 10 minutes. Set aside.
In the meantime, add 2 tablespoons olive oil to saute pan and fry the roasted onions, tomato and peeled garlic for about 1 minute. Add the tortilla and bolillo and cook for 5 minutes, stirring frequently. Add the peanuts, pumpkin seeds, sesame seeds, almonds, raisins, oregano, cumin, thyme, coriander seeds, whole black peppercorns and cinnamon stick. Saute until fragrant and ingredients are slightly toastes, about 8 minutes. Add chiles, draining them of excess soaking liquid and mix into seed mixture
Transfer half of the cooled seed and chile mixture and 1 tomatillo into a high velocity mixer (I have the vitamix). Add ½ cup broth and blend 3 minutes to a very smooth paste, adding more broth if necessary. Repeat with remaining seed and chile mixture and remaining tomatillo.
Heat 2 tablespoons olive oil in heavy large pot. Add mole paste and cook, stirring frequently until darkened, adding more broth to desired consistency. Add sugar and chocolate. Season with plenty of salt and pepper. Make tacos using roasted vegetable pieces, hoja santa, mole, sesame seeds and (plat-based) cream (if desired). Serve!