Roast the Spaghetti Squash: Preheat oven to 400°F (200°C). Cut the squash in half lengthwise and remove seeds. Brush cut surfaces with 1 Tbsp olive oil; season with salt and pepper. Place cut-side down on a parchment-lined baking sheet. Roast for 35-45 minutes, or until tender.
Prepare the Beef Ragu Base: While squash roasts, heat 1 Tbsp olive oil in a large pot or Dutch oven over medium-high heat. Add onion; cook until softened (5-7 min). Add garlic; cook 1 min more. Add ground beef; cook, breaking it apart, until browned (8-10 min). Drain excess fat.
Simmer the Ragu: Stir in tomato sauce, diced tomatoes, tomato paste, Italian seasoning, and crushed red pepper flakes. Bring to a boil, reduce heat to low, cover, and simmer for 20-25 minutes, stirring occasionally.
Finish the Ragu: Stir in balsamic vinegar. Taste and adjust seasoning with salt and pepper if necessary. Keep warm.
Prepare Squash Strands: Once squash is roasted and slightly cooled, use a fork to scrape the flesh into spaghetti-like strands.
Serve: Divide squash strands among six bowls. Top generously with the beef ragu. Garnish with optional fresh basil and Parmesan cheese before serving.