Place all peppers in a very large heat-proof non-reactive container; set aside. In a large nonreactive pot combine the vinegar, water, sugar, pickling spice, and 1/4 cup salt. Bring to boiling, stirring to dissolve sugar. Pour the hot liquid over peppers and stir. Cover with plastic wrap and allow to cool to room temperature. Once cool, place in an air tight container and chill up to 4 hours. Drain, discarding liquid.
Brush meat lightly with oil and season with salt and black pepper. Let stand while preparing coals.
Light natural wood charcoal and allow to get white hot. Spread out in an even layer. Place meat directly on coals and grill for 3 minutes for skirt steak or 5 minutes for flank steak, turning once (use tongs to remove any coals that stick to steak). Remove and wrap in foil. Let stand for 5 minutes. Use a sharp knife to very thinly slice meat across the grain. Serve with peppers.