Place 1 cup yellow split peas in a small bowl and pour in room temperature water to cover. Let soak 30 minutes, then drain and set aside.

Meanwhile, heat a large Dutch oven or other heavy pot over medium. Cook 5 slices bacon, chopped, stirring occasionally, until browned and beginning to crisp, 7–9 minutes. Spoon off all but about 2 Tbsp. fat from pot; discard excess or save for another use. Add 1 small onion, chopped, 2 scallions, thinly sliced, 4 garlic cloves, finely chopped, 2 medium carrots, peeled, chopped, ½ green bell pepper, ribs and seeds removed, chopped, 1 seasoning pepper (pimiento), finely chopped (if using), 1 tsp. Diamond Crystal or ½ tsp. Morton kosher salt, and ½ tsp. freshly ground pepper. Cook, stirring often, until onion is softened and beginning to turn golden, 5–8 minutes. Add 2 plum tomatoes, chopped, ¼ cup green seasoning, and 1 tsp. thyme leaves and stir to coat evenly. Cook, stirring occasionally, until tomatoes burst and break apart and peppers are softened slightly, 7–9 minutes.

While vegetables are cooking, blend 1 cup fresh or frozen corn kernels, a pinch of kosher salt, and ¼ cup water in a blender or food processor until texture is similar to creamed corn; set aside.

Add 2 cups 1" cubes peeled kabocha or butternut squash, one 13.5-oz. can unsweetened coconut milk, 3 cups low-sodium chicken broth, 2 tsp. Diamond Crystal or 1 tsp. Morton kosher salt and reserved split peas to pot. Bring to a boil, then cover and reduce heat to medium-low. Simmer 20 minutes.

While the squash is simmer, make the dumplings if desired, or skip to step 7. Mix 1 cup all-purpose flour and 1 tsp. Diamond Crystal or ½ tsp. Morton kosher salt in a small bowl to combine. Using your hands, work in 5 Tbsp. water, a tablespoonful at a time, until a firm dough forms. Turn out onto a surface and knead until a smooth ball forms, about 3 minutes. Let rest 10 minutes.

Break dough up into 4 equal pieces. Working one at a time, roll each piece on surface with your hands to create a ½"-thick rope. Cut ropes into 1" pieces. Add dumplings to pot and stir to combine. Re-cover pot and cook until dumplings are mostly tender, 13–17 minutes.

Add 2 ears of corn, husked, cut crosswise into 1"-thick rounds and reserved puréed corn to soup; reduce heat to medium and cook until soup is thickened and dumplings are completely tender, 9–11 minutes. Taste soup and season with more salt if needed.

Ladle soup into bowls and serve with Trinidadian hot sauce if you can get your hands on it. Do ahead: Soup can be made 4 days ahead. Let cool; cover and chill. Reheat over medium, thinning with water as need, before serving.