Heat and grease a waffle iron. Heat oven to 250°F. Place a wire rack on a rimmed baking sheet and set aside.
Whisk together flour, sugar, cocoa, baking powder, baking soda, and salt in a medium bowl. In another medium bowl, whisk together eggs, milk, butter, and vanilla. Pour wet ingredients into dry ingredients and quickly combine without over-mixing. Rest batter for at least 15 minutes.
Ladle about ½ cup batter at a time onto prepared iron and cook for about 4 minutes, or until iron signals waffle is ready. Check and cook for another minute if needed. Remove, place on prepared baking sheet, and keep warm in oven until ready to serve.
For Whipped Ricotta: Put ricotta in bowl of a stand mixer fitted with the whisk attachment (or use a hand-held mixer) and beat on medium speed while slowly pouring in cream. Add honey to taste and continue to whip until mixture is smooth and fluffy and ricotta has lost most of its grainy texture. Taste and adjust seasoning as needed.
For Raspberry-Pear Compote:Combine pear, raspberries, orange zest, half the orange juice (reserve remainder for another use), sugar, and rosemary in a medium saucepan over medium-high heat and bring to a boil, then reduce to a simmer. Cook, stirring occasionally, until mixture is thick and syrupy, 5 to 7 minutes.
Discard rosemary. Serve warm over waffles, with dollops of whipped ricotta and an extra drizzle of honey.