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Place a rack in center of oven; preheat to 425°. In a large bowl, whisk vinegar, oil, red pepper, 2 tablespoons honey, and 1 teaspoon salt. Add Brussels sprouts and toss until combined.
Arrange sprouts cut sides down on an unlined baking sheet. Drizzle any remaining liquid in bowl on top.
Roast 15 minutes. Lightly toss sprouts to redistribute, then arrange cut sides down. Continue to roast until tender in the center and crisp on top, 5 to 10 minutes more.
Drizzle with remaining 1 teaspoon honey; season with remaining ¼ teaspoon salt. Toss to combine, then transfer to a platter.