Make the dressing: whisk vinegar, oil, garlic, seasoning, and salt together.
Cut each tomato into four 1/2-inch-thick (1-cm) slices. Place tomato slices and mushrooms on baking sheet lined with parchment paper (start mushrooms gills-up). Brush dressing on both sides of vegetables. Bake 20-25 minutes, turning once. Meanwhile, mix goat cheese with seasoning and divide into 4 portions.
When baking is done, remove from oven. Place a mushroom on each plate, gills up. Top each with two tomato slices, then the basil, then a portion of goat cheese, and finally sprinkle with pine nuts and bread crumbs. Drizzle with additional oil, if desired.