For the Glaze In a medium saucepan, bring the stout, brown sugar and honey to a boil. Reduce the heat to medium and cook until reduced by half, stirring occasionally. Remove from the heat and allow the mixture to cool.
Heat 2 Tbs. of the oil in a 10- to 12-inch skillet over medium-low heat. Cook the onion, carrots, celery, stirring frequently, until softened and just beginning to brown, 6 to 8 minutes. Add the garlic and cook for 1 minute more. Add the stout and simmer briskly until almost dry, about 4-5 minutes. Transfer to a large bowl and let cool until just warm.
Soak the bread in milk until soggy but not falling apart. Lightly squeeze out some of the milk. Finely chop and add to the vegetable mixture.
In a small bowl, reconstitute the dried mushrooms by covering them with boiling water; allow to soak for 8-10 minutes, stirring occasionally. Drain the mushrooms and finely chop.
Add the beef, veal and eggs to the vegetable mixture. Scatter the cheddar, rehydrated mushrooms, parsley, salt and pepper over the meat, and then sprinkle with the Worcestershire sauce. Gently mix all the ingredients until just combined; try not to compact the mixture too much as you do this.
Line a large rimmed baking sheet with aluminum foil, then a sheet of parchment paper. Transfer the meat mixture to the sheet and form into a 9x5-inch rectangular loaf. Drape the meatloaf with slightly overlapping strips of bacon, tucking the ends under the loaf. Brush the top of the meatloaf with half of the glaze. Save the rest for later.
Bake in 375 degree preheated oven for 50-55 minutes. If using a meat thermometer it should be at 160 degrees in the center of the meatloaf.
Remove the meatloaf from the center of the oven and place the oven rack 6 inches from the broiler element and preheat the broiler. Brush the remaining glaze over the meatloaf and broil until the bacon is browned and crisped, about 2-3 minutes, checking and rotating to make sure the glaze doesn't scorch. Transfer to a serving platter and let rest 10 minutes before cutting.