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SUBMIT YOUR IDEAI originally solved it using Append Field and Distance tools, but the result was off for certain items. Since I couldn't find the reason, I took a peek at other solutions and found out how to use Find Nearest. Turns out my original solution was fine, but I used Required vs. Assigned for my total UnitMiles Formula, thus impacting my totals. I had assumed that the Required and Assigned were the same, which is something I should double-check next time.
Finally getting around to tackling spatial toll pallet - weekly challenges a great resource to apply learnings.
Tricky... but done!