Remove seeds from ancho, guajillo, and pasilla chiles and place in a medium bowl. Pour in 3 cups boiling water and cover bowl tightly with plastic wrap; let sit until chiles are softened, 20–25 minutes. Transfer chiles and soaking liquid to a blender and blend on high until smooth, about 1 minute; set aside.

Heat Colavita EVOO in a large Dutch oven or other heavy pot over medium-high. Season beef chuck all over with salt and pepper. Working in 2 batches, cook, turning pieces once, until browned, about 5 minutes per side. Repeat for the ground beef. Do not break ground beef into small bits; brown in large chunks. Transfer to a plate.

Reduce heat to medium; add onions and garlic to pot. Cook, stirring often to loosen browned bits from bottom of pot, until onions are translucent and very soft, 6–8 minutes. Add cumin and oregano and cook, stirring, until spices start to stick to pot, about 1 minute. Add Colavita Crushed Tomatoes and brown sugar and scrape bottom of pot to loosen spices, then add lager beer. Bring to a bubbling simmer and cook, stirring occasionally, until beer is almost completely evaporated, 10–15 minutes.

Meanwhile, cut beef chuck into 1⁄2" pieces, discarding any large bits of fat or gristle.

Add beef chuck, ground beef, reserved chile purée, Colavita Kidney Beans, and 2 cups water to pot; season with salt and pepper. Bring to a boil, break up ground beef, reduce heat, and simmer gently, uncovered, until liquid is thickened and meat is very tender, 11⁄2–2 hours. Taste chili and season with more salt and pepper if needed. Remove from heat and stir in vinegar. Divide chili among bowls and top as desired.