Step 1Place the roasted bell peppers, dried ancho chiles and sugar in a medium, heavy-bottom sauce pan. Simmer uncovered over low heat until the chiles are very soft and most of the liquid is evaporated, about 1 hour, 15 minutes. Stir in the balsamic vinegar, remove from heat and cool.
Step 2In a blender, or with a hand-held blender, puree the ancho-pepper mixture. (This makes 1 cup ancho-pepper puree, more than is needed for the chutney. It will keep in the refrigerator, covered, for up to 2 weeks.) Fold one-fourth cup of the puree (add more to taste) into the cranberry sauce. This makes more chutney than is needed for two sandwiches; keep covered in the refrigerator for up to 2 weeks.
Step 1Heat the oven to 375 degrees. Place the kabocha cut side down on a cutting board and cut away the thick skin with a knife (or also use a peeler for harder-to-cut spots). Cut the squash into about half-inch strips and toss them with the oil, brown sugar and salt.
Step 2Place the squash on a parchment-lined baking sheet and roast in the oven until the squash is soft and caramelized, about 35 minutes.
Step 3In a food processor, puree the squash until smooth, adding a bit of water if necessary. Cool the puree and fold it into the creme fraiche. This makes about 1 1/2 cups spread, more than is needed for this recipe. It will keep, covered in the refrigerator, for up to 5 days.
Step 1Spread a generous layer of roasted kabocha spread on one side of two slices of bread and a layer of ancho-bell-pepper-cranberry chutney on one side of the remaining slices of bread. Put several slices of turkey breast on top of the chutney. Divide the bacon between the two sandwiches, placing it on top of the turkey. Top with the romaine and invert the bread slices with the kabocha spread over the rest of the sandwiches. Serve immediately.