Preheat oven to 400°.
Set a wire rack in a foil-lined rimmed baking sheet. Lay bacon slices on the rack.
Bake bacon at 400° for 10-12 minutes, until edges are barely crisp; chewy centers will be easier to skewer. Leave oven at 400°.
While bacon is baking, heat oil in a medium pan over medium-high heat. Saute onion and garlic until onion is translucent, then transfer to a mixing bowl.
Add beef, worcestershire, salt, & pepper to the onions and mix well.
Remove the rack of bacon from the foil-lined baking sheet. Roll beef into 24 small meatballs and set on the baking sheet.
Bake meatballs at 400° for 10-12 minutes, until browned.
While meatballs are baking, slice cherry tomatoes in half widthwise. Slice each bacon strip into 4 pieces and scoop a teaspoon of guacamole onto each piece. Cut monterey jack into 8 slices, then cut each slice into 3 squares. If using jalapeños, cut thinly into 24 slices.
Skewer one cherry tomato half, guacamole-topped bacon slice, jalapeño slice, cheese slice, meatball, and finish with another cherry tomato half. Repeat for all 24 skewers.
Whisk together all sauce ingredients or pulse in a food processor.
Serve skewers warm with chipotle dipping sauce.