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In a large skillet over medium-high heat, heat oil. Prick sausages with a fork and brown on all sides until cooked through, 5 to 8 minutes. Transfer to a plate to rest for 2 to 3 minutes, then cut into ¼" slices on a diagonal. Set aside.
Meanwhile, in a sauce pan over medium heat, warm tomato sauce, garlic, and chili powder. Simmer for 2 minutes and keep warm.
In a large skillet over medium-low heat, drizzle olive oil and add 1 flour tortilla; fill half the tortilla with a handful of Monterey Jack, a layer of sliced sausages, and more cheese, then fold tortilla over to create a half moon. Cook until cheese is melted. Repeat for remaining tortillas.
Top each quesadilla with spicy tomato sauce and Cotija and garnish with parsley. Serve immediately.