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Step 1: Heat 2 T of the olive oil in a large saute pan over medium heat. Add half the asparagus pieces and saute 3 minutes; remove to a bowl. Saute remaining asparagus; remove to bowl and set all aside.
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Step 2: Wash, stem and slice baby portabellas. Set aside.
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Step 3: Combine the port and sherry in a small saucepan. Simmer over medium heat until only 1/2 c remains, about 15 minutes. Add the cream and simmer for 5 minutes. Set aside.
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Step 4: Preheat oven to 350.
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Step 5: Split top of lobster tail shell and pull lobster meat out, leaving it attached at tail end. Push shell back together and rest meat on top of it. Push skewer through meat, front to tail end, to keep it from curling during cooking process. Set aside.
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Step 6: Heat 2 T of the olive oil in large saute pan until it smokes. Saute the sliced mushrooms a few minutes and transfer them to sherry mixture. Simmer over low heat for 3-4 minutes, then remove from heat and set aside.
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Step 7: Make mashed potatoes.
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(Can make everything ahead to this point. Rewarm to serving temperature and have ready to serve when lobster tail is ready to serve.)
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Step 8: Put hot water in bottom of broiler pan. Set lobster tails on broiler rack. Brush with melted butter and sprinkle with paprika. Tent loosely with foil. Bake at 350 for 25-30 minutes. Remove foil tent and broil 1-2 minutes. Cut lobster meat away from shell.
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(This is a wonderful, failproof method for making lobster tail. Always stays moist; never rubbery.)
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Step 9: To serve, make bed of mashed potatoes on each plate. Top with mushroom-sherry-cream mixture, then asparagus, then lobster. Spoon extra sauce over and around, if desired.
