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Bring large pot of salted water to a boil. Cook tortellini until al dente, according to package instructions. Drain and set aside. Cover with olive oil to prevent sticking.
Heat large Dutch oven over medium-high heat. Add guanciale and cook until crispy and fat has rendered. Crumble sausage into pot and cook, breaking into smaller pieces with spoon, until browned and cooked through, about 5 minutes. Remove and set aside.
In same pot, add onion, garlic and thyme. Sauté until onion becomes translucent, 2 to 3 minutes. Pour in wine to deglaze pot, scraping up any brown bits, and simmer until reduced by half. Add cream and simmer until reduced by half again. Pour in chicken stock and bring back to a simmer. Add cooked sausage and Parmesan, and simmer uncovered for 30 minutes.
Five minutes before soup is finished, add rapini to become tender and tortellini to heat through. Season soup with salt and lots of pepper. Garnish with additional Parmesan and pepper.
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