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This has been fixed with the help of @Sean Yen and @OoeyGUI. @Sean Yen worked through the issue with me via this GitHub issue report.
Short story: The following command fixed my install
choco upgrade -y --force ros-melodic-desktop
Afterward I noted that the command to install ROS for Windows under the Binary Package Installation section here changed from:
choco upgrade ros-melodic-desktop -y
to
choco upgrade ros-melodic-desktop_full -y
so it might have stemmed from not downloading the full package on the initial install.