Michael’s Theater Tour Shepherd’s Pie

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About 200 years ago, I won a collegiate playwriting contest,for which the prize was $1,000.  Myex-wife and I used that money to go on a "Theater Tour" of London andenvirons ...during which glamorous visit I first tasted old-school Shepherd'sPie.  In those days, it wasn't as easy tofind recipes, never mind popping online to find dozens of variations...so, whenI got home, my ex and I came up with this recipe, which is in my opinion a verytasty replica of the Pub-style working man's Shepherd's Pie we had Over There.
The nutrition facts include the mashed potato recipe below and were created at Calorie Count! This dish will be easy to adjust downward for sodium and fat if you makea simple potato and buttermilk mash-up. Or just use a bit less butter and use your favorite salt substitute.
Michael’s TheaterTour Shepherd’s Pie
Ingredients:
3 Tbsp. extra-virgin olive oil 3 Tbsp. unsalted butter 1 medium onion, diced 3 medium carrots, peeled and sliced 1 rib celery, sliced 1/2 pound small crimini mushrooms, quartered 2 cloves garlic, minced 1 Tbsp. kosher salt, divided3/4 tsp. dried oregano1 tsp. brown sugar  3 Tbsp. tomato paste 1 pound lean, trimmed beef, cut into 1” chunks 1 cup sifted all-purpose flour1/2 cup Guinness Stout (or canned low sodium beef broth)1/2 tsp. Worcestershire sauce freshly ground black pepper 4 cups mashed potatoes, Michael’s recipe follows thedirections for meat.3/4 cup grated Cheddar and/or Stilton cheese
Directions:
Preheat oven to 375°.
Cut the well-trimmed beef into short strips, as you wouldfor stroganoff.  Place the beef into alarge, sealable plastic bag with the flour, 1/2 Tbsp. salt and blackpepper.  Seal the bag and shake the beefuntil it is coated with the flour mixture.
Heat the olive oil and 1 Tbsp. butter in a large skilletover medium heat.  Place the floured meatin the skillet and brown on all sides. Remove and set aside to drain. (If using Guinness, add a splash to the hot skillet and scrape theskillet to loosen the meat residue before adding veggies!)  Add the onion, oregano, garlic, celery andcarrots to the skillet and cook until vegetables begin to soften, about 6minutes.  Add a bit more olive oil ifnecessary.  Stir in the tomato paste,brown sugar and mushrooms, cooking for about 8 more minutes, until mushroomsare soft and tomato paste has turned brick red.
Stir in the Guinness (or broth), the remaining salt, theWorcestershire, a bit more pepper, and the drained beef, stirring until thealcohol has cooked out of the liquid. (Discard the remaining flour.)
Transfer the meat and vegetables to a 2-quart oval casseroledish and spread the mashed potatoes over the top, leaving a 1/4-inch borderaround the edge.  Sprinkle with thegrated cheese, and dot with the remaining butter.  Bake until potatoes brown lightly and thejuices bubble around the edge, about 40 minutes.  Let cool for 10 minutes before serving.
Mashed Potatoes
Ingredients:
1-1/2 lbs. Yukon gold potatoes, quartered (peels left on ifdesired) 2 tsp. kosher salt, plus more for seasoning 3/4 cup whole milk    6 Tbsp. unsalted butter 2 Tbsp. chopped fresh flat-leaf parsley freshly ground black pepper
Directions:
Put the potatoes in a saucepan with cold water to cover byabout 1-inch and add the salt.  Bring toa simmer over medium-high heat, uncovered, until the potatoes are tender butnot mushy, about 15 minutes.  At the sametime, combine the milk and butter in a small saucepan and warm over low heatuntil the butter is melted. Remove from the heat and cover to keep warm.
Drain the potatoes and return to the saucepan.  Toss the potatoes over medium heat untildry.  Add the heated milk mixture andmash the potatoes until just slightly chunky, then stir in the parsley andseason with salt and pepper, to taste.