Adding to my initial post, I think the issue is related to this change in Windows: https://www.bleepingcomputer.com/news/microsoft/microsoft-driver-update-change-may-break-windows-10-plug-and-play/
The article at https://learn.microsoft.com/en-us/windows-hardware/manufacture/desktop/add-and-remove-drivers-to-an-offline-windows-image (from 2018) states:
"When you use DISM to install a device driver to an offline image, the device driver is added to the driver store in the offline image. When the image is booted, Plug and Play (PnP) runs and associates the drivers in the store to the corresponding devices on the computer."
The article Iinked further up says that Plug and Play may no longer assign drivers to new hardware like it used to in the past. However, it also says that this is dictated by how each driver is programmed -- "automatic" drivers will apparently still be installed when new hardware is discovered by Windows, but "manual" drivers will not. I think that the drivers I have (which includes Intel/Nvidia graphics, Intel WiFi/BT, and chipset drivers) are "manual" and that's why Windows 10 2009 skips them if the machine was sysprepped/generalized once.
The drivers are in fact activated on the very first boot of the 2009 image (assuming I had integrated the drivers with DISM). Only after that process, if I add new drivers offline via DISM and re-deploy the image, PnP doesn't activate them.
I'm not sure that the answer given by TeemoTang will fix this but I will try anyway.