Preheat oven to 425f°
Combine strawberries, sugar, salt, pepper and olive oil in a bowl, toss to coat. place on foil-lined tray, and roast for approx. 20 minutes.
While strawberries are roasting, combine shallots, balsamic vinegar, white wine vinegar, dijon mustard, maple syrup, salt & pepper in mixing bowl.
Add strawberries (allow to cool first) into bowl, get as much of caramelized drippings as possible, and then blend with processor, either to smooth puree or a little chunky per your preference.
Once all other ingredients are mixed in to preference, slowly add in 1/4 cup olive oil.
Add 3-4 TBSP into mixed greens/veggies salad to taste, toss and serve.