Preheat oven to 450.
Cut squash in half through pole, scoop out seeds and pulp (a melon baller works well here). Lightly cover cut surface of squash with olive oil and sprinkle generously with salt and pepper. Place, cut side up, on baking sheet and put in oven. Roast until flesh can be easily pierced with a fork, 20-40 minutes depending on size. Allow to cool slightly.
While squash is roasting, toss tomatoes with olive oil (just to coat), salt and pepper, herb of your choice and sugar. Spread on baking sheet and place in oven. Roast until tomatoes are lightly charred and bursting, about 20 minutes. Remove from oven, dump tomatoes in large bowl and toss with minced garlic. The heat from the tomatoes will soften and mellow the garlic.
When squash is cool enough to handle (a dish towel or oven mitt is helpful here) put one half in your hand and using a fork scrape strands of spaghetti squash into bowl with tomatoes. Repeat with other half. Toss well, drizzling with olive oil as desired.
Plate, with optional shrimp or burrata on top, grate fresh parmesan over all and sprinkle with basil.