I'm slightly confused. here. You say the device has USB host and you want to connect more than one client device through a hub. This is definitely supported by the OS, and I've done this with several devices from several manufacturers, though never with a Nomad. Not sure what the OEM is talking about with "resource conflicts" as the USB spec itself allows for multiple devices (kind of the whole point behind a "bus").
But you say that your second "device" is the debugger. That isn't a USB Host connection from the device perspective, that's a USB Client connection, and it typically uses completely different hardware and drivers for that connection. Can a device have both a host and a client connection? Again, yes I've done this with many devices (but not a Nomad) and the OS fully supports it.
Now maybe this is USB OTG hardware (though back in the 5.0 days I doubt it) and the OEM didn't do the design well to handle a client and a host at the same time. Maybe the physical hardware is laid out poorly or the OAL portion of their USB driver is poorly done and can't route properly through a hub properly (I've definitely seen that before). Hard to say.
A USB Analyzer would tell you a whole lot about what's actually happening and where the problem is, but it is definitely a supported scenario by both the USB spec and the OS. If it's failing, it's a manufacturer/device-specific problem.