Make the blueberry maple bourbon sauce: In a small saucepan, stir together the blueberry jam, maple syrup, and water. Bring to a simmer over medium heat and cook until slightly thickened, about 5 minutes. Add the bourbon and continue simmering for 1–2 minutes, until the alcohol cooks off. Remove the pot from heat and stir in the vanilla, salt, and pepper. Set aside until ready to serve. If making ahead of time, cover and refrigerate for up to 1 month. Re-warm before serving.
Make the Brie sticks: Line a baking sheet with parchment paper.
Cut each Brie wheel into ½-inch-wide sticks. Transfer to the prepared baking sheet and refrigerate while you prepare the breading station.
Add the butter crackers to a food processor and process into fine, uniform crumbs. Transfer to a wide, shallow bowl.
Add the eggs and flour to 2 separate wide, shallow bowls.
Dredge each Brie stick in the flour to coat completely. Coat in the egg, ensuring there are no visible dry spots, then roll in the cracker crumbs to coat. Dip again in the eggs and cracker crumbs. Freeze the Brie sticks for at least 30 minutes, up to overnight.
Heat the vegetable oil in a wide, shallow pan over medium heat until the temperature reaches 375˚F (190˚C). Set a wire rack over a baking sheet.
Working in batches to avoid overcrowding the pan, fry the Brie sticks in the hot oil until golden brown, 1–2 minutes. Transfer to the wire rack and immediately sprinkle with salt.
Serve the Brie sticks hot with the warm blueberry maple bourbon sauce and bacon jam alongside for dipping.