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I use group policy to enforce via Restricted Group who is in the local administrators group. However, some users we have deemed should be a local admin on their machine and they drop out of the local administrators group when the next group policy update takes place. How can I add a user to the local administrators group and prevent it from being overwritten by the Restricted Group?

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Your policy is doing what it is supposed to be doing. You need an exclusion to the policy - effectively denying the policy from running on your specific computer - or an update to your methodology. My preferred method in a case like this is utilizing group policy preferences for group memberships... it's a lot more flexible.

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