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Notice how different records have different properties to be updated. When I call the bulk upsert function it converts data set into a CSV. The first record of the upsert only has a single property. So the csv ends up looking something like:
property1
'w'
'x'
'z'
As a result, property 2 on the second record and property 2 and property 3 on the third record never get updated.
It looks like there's a built in assumption that all records have the same properties set on an upsert. This is definitely not true in my use cases.
A mini work around is to always have a dummy record at the beginning of your list which has all properties.