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In a medium bowl, soak cashews in 4 cups water for 1-3 hours.
Preheat oven to 400 degrees (F).
Prepare potatoes by poking each potato 4 times with a fork, rubbing with olive oil, and seasoning with salt. Place directly onto oven rack and bake for 50-60 minutes.
Prepare garlic for roasting by slicing the half head of garlic width-wise, wrapping in foil, and placing on the oven rack. Roast for 40 minutes.
While potatoes and garlic cook, make red sauce by heating 2 tablespoons olive oil in a medium saucepan, adding onions and salt, and sweating for 5 minutes. Add garlic and cook for an additional 1-2 minutes. Add oregano, thyme, fennel seed, black pepper, tomatoes, and additional salt. Simmer for about 25 minutes.
Make roasted broccoli by cutting into small florets, tossing with olive oil and salt, and baking in the oven for 10-15 minutes.
Remove potatoes from the oven, cut in half length-wise, scoop out flesh, brush with olive oil, season with salt, and return to the oven for 10-15 minutes.
Make cashew cheese sauce by blending soaked/drained cashews with roasted garlic, water, and salt until smooth.
Assemble the potato skins by dividing red sauce between potato halves, topping with cashew cream and roasted broccoli, and heating in the oven for 5-10 minutes.