Just to confirm, if I reimage a remote/off network client and it needs a license, can I connect it to ICG and it obtain a license?

Yes, connect through ICG and it should then grab a license from your UMS <=>ILP
Is there any way to script the ICG connection settings in an install from USB?
Well, yes even if not completely through GUI:
on OSC default USB Config: let‘s say a preconfiguration, not really a profile: Start the OSC, and click on Edit. There you can preset a config that will apply on every install.
On ICG join: github.com/IGEL-Community/IGEL-Community.github.io/wiki/Scripts:-Custom-Commands#icg-automatic-registration
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