Pineapple Upside-Down Cobbler

"Tender cake houses jammy sour cherries and chunks of sweet pineapple in this cobbler meets upside down cake hybrid...."

INGREDIENTS
¾ cup (1½ sticks) unsalted butter, melted
3⅓ cups (417 g) self-rising flour
2½ cups whole milk
1½ tsp. Diamond Crystal or 1 tsp. Morton kosher salt
2½ cups plus 2 Tbsp. (525 g) granulated sugar
36 drained sour black cherries in syrup (such as Amarena; about 1 cup), divided, plus more for serving
3 cups drained crushed pineapple, divided
½ cup (100 g) raw sugar
2 cups heavy cream
2 tsp. vanilla extract
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