Place warm water, sugar, vegetable oil, salt, Italian seasoning, bread flour and active dry yeast in the pan of your bread machine in the order recommended by the manufacturer. If yeast is last, make a small well in the flour and add the yeast there. Place bread machine on dough cycle setting and let run through completely.
Once the dough cycle is complete, remove dough and place it on a floured bread board. Roll out into a 12x20 inch rectangle (or best you can).
In a small bowl combine melted butter and minced garlic. Brush butter mixture all over the entire dough rectangle. Sprinkle sliced olives, 1 1/2 cups shredded cheese and bacon crumbles evenly over the dough.
(This is where I follow Joy the Baker's Instructions for slicing and stacking. She has great step by step photos on her Cinnamon Sugar Pull Apart Loaf if interested).This is also where I recommend to get another set of hands to help stack and hold. Prepare your loaf pan by spraying with non stick cooking spray or brush with melted butter.
From Joy: Slice the dough vertically, into six equal-sized strips. Stack the strips on top of one another and slice the stack into six equal slices once again. You’ll have six stacks of six squares. Layer the dough squares in the loaf pan like a flip-book.
OK back to Kristen: Remove all but the bottom rack of your oven and preheat oven to 350°F. Once preheated, place bread loaf into the oven and bake for 30-35 minutes. During the last 5 minutes, add the remaining 1/4 cup of shredded cheese. Bake until cheese is melted and bread is golden brown in color. Do not underbake.
Remove from the oven and allow to rest for 10 minutes. Gently invert the loaf onto a serving plate. Place in front of your guests and watch them pull apart and marvel at your amazing baking skills! Best if eaten warm, the same day.