Nuevo Chipotle Beef in Butternut Squash Boats

The other day(about two months ago) I was watching Food Network's Cook off Challenge when a recipe caught my eye and I thought--I should try to make that. It looked so delicious and different from anything I usually cook. So I finally got around to getting the ingredients for it and may I say it's my favorite thing I have ever cooked without knowing what it would taste like at all beforehand. Recipe by Christine Riccitelli.

Ingredients
1 1/2 lbs stew beef
1/3 cup water
1/4 cup tomato paste
2 Tbs. brown sugar
2 Tbs. balsamic vinegar
2 tsp. chili pepper
1 tsp. ground cumin
1/2 tsp. salt
1/2 tsp. ground pepper
1 medium butternut squash, cut into quarters and remove seeds
1 1/2 cups water

Optional (but highly recommended)
1 med. tomato (chopped)
1 small avocado (cut into cubes)
1/4 cup freshly chopped cilantro leaves

Directions
1.. The directions called for this mixture to be cooked in the oven in a stockpot for 1 hr 45 min t0 2 hours and 15 min @ 325 degrees, however I cooked it on the stove top for 2 hours on medium heat while covered. Combine beef, water, tomato paste, sugar, vinegar, chili pepper, cumin, salt, & pepper and cook until tender.
2. While meat is cooking put squash cut side down in a 13x9 pan with the water at the bottom. Cook in oven @ 325 degrees for at least an hour until the squash is fork tender. Halfway through I flipped the squash.
3. Place squash on plate and put beef picture on top and garnish with cilantro, tomato, & avocados.