Oil three 9" round cake pans and line with parchment paper.
Peel and dice 2 pears and set aside.
Mix cake mixes and puddings together.
Whip in eggs. Add oil, milk and vanilla extract.
Stir in pecans, 1/2 cup chocolate chips and diced pears.
Pour evenly into three cake pans.
Bake for 35 to 40 minutes, checking with a toothpick to see if done.
For the Frosting
While cake is baking, add butter to a medium bowl and whip till fluffy about 1 minute.
Add sugar a couple of spoonfuls at a time
Add cream and vanilla. Set aside.
For the Caramel Drizzle
Using a small saucepan, melt sugar into water at medium heat. Cook about 5 minutes, stirring until sugar is melted.
At this point take off heat and add cream. Stir until incorporated. It will bubble profusely.
Put back on heat but lower it to medium-low. Cook for about 15 min or until the candy thermometer reads 250. Remove from heat, add vanilla and then butter, one tablespoon at a time.
Mixture will thicken as it cools, so do not wait too long to drizzle on the cake.
Putting it all together
First melt 1 1/2 cups chocolate chips in a microwaveable bowl by placing in microwave for 30 seconds.
Take your third pear and dip it in the caramel sauce. Lean the pot to one side, dip the pear in and twirl it around until the entire pear is coated. Drizzle melted white chocolate on the pear with a spoon. Set aside.
Place first cake on a plate. Cover in thin layer of caramel. Spread a thin layer of frosting over the caramel. Repeat.
On top layer after icing the cake, drizzle over caramel and white chocolate. Place pear on top.