Local Pickup and Free Shipping Not Both Displaying

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I'm testing the new Shipping Profiles and playing with my shipping options. I noticed an error.
My store offers local in store pickup for free.

My store also offers free shipping over $100 on most items.

If I fill my cart with over $100 of items, when I use an out of state shipping address, everything works as intended.

 

However, when I use an in state address, only Local Pickup displays. It does not show the free standard shipping for over $100 option. Some of the local guys may want things shipped to their house, but currently they'd have to pay for ground shipping to do that, or select the local pickup option and message us to say to ship it. Is there a workaround for this?

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