In a small bowl, dissolve yeast in warm water. Set aside. In a large mixing bowl, combine the milk, pumpkin, butter, sugar, salt, and pumpkin pie spice.
Beat in eggs and dissolved yeast mixture. Add 2 1/2 cups of flour and mix until just combined. Add the remaining 2 - 2 1/2 cups flour until dough is no longer sticky.
At this point either change to the kneading attachment on your mixer or turn onto floured surface; knead until dough is smooth and elastic, about 3-5 minutes.
Place dough in a bowl coated with cooking spray, turning once to coat entire surface of dough. Cover and let rise in a warm place for 1 hour or until doubled in size.
Meanwhile, make caramel by combining butter, heavy cream, brown sugar, corn syrup, and vanilla in a medium saucepan. Bring to a boil over medium heat and cook, continuously stirring, until caramel has reach 210-215 degrees F (about a minute after boiling). Pour half of caramel into a greased 10-inch fluted pan. Sprinkle half of the pecans over caramel.
Punch down dough and shape into 40 balls (about 1-inch diameter). In a small bowl, combine sugar, cinnamon, and pumpkin pie spice.
Place melted butter in another bowl. Roll balls in butter, then roll in sugar mixture. Place 20 balls in the pan over the caramel. Top with remaining caramel and pecans.
Roll remaining balls in butter and sugar and place over balls in tubed pan. Let stand for 20 minutes.
Place fluted pan on a baking sheet and bake at 350 degrees F for 30-35 minutes or until top is golden brown. Cool bread in the pan on a wired rack for 10 minutes before inverting onto a serving plate. Serve warm.