To prepare dough, dissolve yeast in warm water in a large bowl; let stand 5 minutes. Add 1/2 cup warm milk, granulated sugar, 1/4 cup butter, 1 teaspoon vanilla, salt, and egg; stir with a wooden spoon until combined (batter will not be completely smooth).
Lightly spoon flour into dry measuring cups; level with a knife. Add 3 cups flour to yeast mixture; stir until a soft dough forms. Turn dough out onto a lightly floured surface. Knead until smooth and elastic (about 8 minutes); add enough of remaining flour, 1 tablespoon at a time, to prevent dough from sticking to hands (dough will feel slightly tacky).
Place dough in a large bowl coated with cooking spray; turn to coat top. Cover and let rise in a warm place (85°), free from drafts, 1 hour or until doubled in size. (Press two fingers into dough. If indentation remains, dough has risen enough.)
To prepare filling, combine raisins, brown sugar, and cinnamon. Roll dough into a 15 x 10-inch rectangle; brush with 2 tablespoons melted butter. Sprinkle filling over dough, leaving a 1/2-inch border. Beginning with a long side, roll up dough jelly-roll fashion; pinch seam to seal (do not seal ends of roll). Wrap roll in plastic wrap; chill for 20 minutes.
Unwrap roll, and cut into 20 (1/2-inch) slices. Arrange slices, cut sides up, 1 inch apart on a jelly roll pan coated with cooking spray. Cover and let rise in a warm place (85°) free from drafts, 1 hour and 15 minutes or until doubled in size.
Preheat oven to 350°.
Uncover dough. Bake at 350° for 20 minutes or until rolls are golden brown.
To prepare glaze, combine powdered sugar, 2 tablespoons milk, and 1/2 teaspoon vanilla, stirring well with a whisk. Drizzle glaze over warm rolls.