Preheat the oven or grill to 350 degrees. Lightly coat the bottom of the baking dish with the butter.
Heat 1 tablespoon of the olive oil in the pan over medium-low heat. When the oil is warm, add the pine nuts and stir constantly until toasted, 1-2 minutes. Remove them from the pan, then wipe out the pan with a paper towel if there are any burned pieces.
Turn the burner up to medium-high heat and add the additional tablespoon of olive oil to the pan. Add the onion and celery and cook, stirring frequently until soft, 5-8 minutes. Remove the vegetables from the pan, wiping it out again if necessary, and add the sausage. Cook over medium heat, using a spatula or wood spoon to break up the sausage into small pieces.
When the sausage is no longer pink--about 4-6 minutes into cooking--remove it from the pan. (If you want to limit the grease in the stuffing, place the sausage in a sieve or colander over a bowl and allow the fat to drain from the meat.)
Place the pan back on the burner and increase the heat to high. Add ½ cup of the stock and using a flat spatula, scrape the caramelized bits off the bottom of the pan. (Known as fond, all of that caramelized goodness that is stuck to the bottom of the pan will help flavor the stuffing.)
Add the additional 1 1/2 cups of stock and turn off the heat. Pour the bread cubes into the pot. Add the pine nuts, onion and celery mixture, the sausage, and the dried cherries into the bread mixture.
Using your hands or a large spoon, gently mix the bread cubes with the other ingredients to combine. Most of the stock will absorb into the croutons, but it’s ok if there is still some sitting at the bottom of the pan. Taste the bread cubes with a little bit of sausage. Add salt and freshly ground pepper if desired.
Pour the stuffing into the prepared baking pan and add any remaining stock to the pan. If you like your stuffing to be a little bit gooey, drizzle another 1/2 cup of stock over the top. Cover the baking dish with a sheet of aluminum foil tightly. (To prevent the stuffing from sticking to the foil, you can lightly butter the area of the foil that will touch the stuffing.)
Bake for 20 minutes, then remove the foil and bake another 10-20 minutes until the stuffing is cooked to your liking. Alternatively, allow the stuffing to cool before adding it to the inside of the bird to roast.
Allow to cool for a few minutes before serving or cover it again with foil and keep it warm in a 200 degree oven for up to 30 minutes.