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Some more details I found. It appears to apply them in the same order (not in category order) every time no matter if I do one column /tag category at a time or all at the same time. The PowerCLI display shows them being applied in correct order, but the vsphere side shows them in different orders on each VM.
Name Port User
---- ---- ----
10.10 443 VSPHERE.LOCAL\Admin
.... Assigning Microsoft SQL Server 2016 Ent in Category of Database to ncdad
.... Assigning None in Category of Database to nccvr
.... Assigning Dev in Category of Environment to ncdad
.... Assigning Dev in Category of Environment to nccvr
.... Assigning Analytics in Category of Project to ncdad
.... Assigning Infrastructure-Test in Category of Project to nccvr
.... Assigning None in Category of Software to ncdad
.... Assigning Various Tools in Category of Software to nccvr