Heat milk until warm to touch, 110-115°F. Add to bowl of stand mixer with paddle attachment. Stir in yeast and 1 tablespoon granulated sugar. Let stand 5 minutes, mixture will start to look frothy.
Whisk eggs with vanilla, then add to mixer bowl. Add remaining sugar, butter, oil and orange zest. Mix on low speed until combined.
Add 2 cups flour and kosher salt, stir on low speed until incorporated. Scrape bowl and switch to dough hook attachment. Gradually add remaining 2 cups of flour and continue to mix 2 minutes on low/med speed.
Add dried cherries, craisins, ginger, and pecans; mix until just incorporated. Dough will be sticky.
Turn dough on to lightly floured surface and use a dough scraper to help knead until dough has smoothed out and becomes more elastic, about 2-3 minutes. Form dough into a ball and place in lightly greased large bowl, turning dough to oil top. Cover and let rise at room temperature until doubled, about one hour.
Make the coating: Add sugar, cinnamon, and kosher salt to a jar or covered container and shake to combine. Pour into shallow bowl. In a separate shallow bowl, melt butter in microwave.Spray a 9¾-inch or 10 to12 cup Bundt pan with non-stick cooking spray.
Forming the monkey bread: Punch down dough and turn out onto clean countertop. Pat out dough to approximately a 14-inch round. Using a bench knife, cut dough in to 1½ inch strips, then cut 60-70 one-inch pieces. Roll each piece of dough in to a ball, dip in melted butter, then roll generously in cinnamon sugar.
Layer balls in prepared Bundt pan. Cover and let rise 20 minutes. Adjust oven rack to lower third position. Preheat oven to 350°F while bread is rising.
Bake in preheated oven for 35 minutes. Cool in pan 10 minutes, then invert on serving platter.
Make the glaze: Stir together powdered sugar, orange juice, orange zest, and butter. Drizzle over warm monkey bread and serve.