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After halfway completing this post yesterday I ended up finding the answer. The fields that I was attempting to use logical statements on were configured with Domains or a List of Values. When you configure using these fields everywhere else in the platform the domain alias is displayed in the filter or function, but when you configure using Arcade or ...
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The only way to add a layer using Python/arcpy to ArcMap is using the arcpy.mapping.AddLayer function. This function works with mapping layers.
No matter what you do in the ArcGIS for Python API, you'll never get back an arcpy mapping layer object. Meaning: you cannot simply do a search using the Python API, and pass that reference through to arcpy.mapping....
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