Just to be sure that we have all the information.
I assume that your Brennan B2 is a new unit and not one with 3 USB ports at the back (older models have USB A, USB B and USB C) if it is an older model the USB B port is non functional and should not be used.
Next there is a difference in the power available to USB A and USB C in a normal, functional B2. USB A has the most power
A normal, functional B2 should work with the WiFi dongle in either USB port.
To summarise your issue
1) your WiFi Dongle works in USB A not C
2) your WiFi Dongle does not work in USB C
3) A USB thumb drive with a status light does light up when plugged into USB A
4) A USB thumb drive with a status light does light up when plugged into USB C
5) When plugging a externally powered (with the power connected) USB Hub into USB C, plugging the WiFi dongle into that and powering up the B2 - the WiFi dongle is not recognised.
6) When plugging a externally powered (with the power connected) USB Hub into USB C, plugging an External USB drive into that and powering up the B2 - the External USB drive is not recognised.
If the above is correct the the WiFi Dongle is not the problem.
If the above is correct there is indeed something wrong with the B2's USB C port.
The fact that it appears to be powered shows that it is connected internally (the B2's USB ports are taken off the USB ports on the Raspberry Pi mother board but the connections are not direct and are shared with the Brennan's internal drive system). There could be a loose connection causing the issue (hence Daniels suggestion above).
The other possibility is that the B2 software is corrupt (this is held on a small internal SD Card separate from the HDD on which it stores music) - This could be tested by re-flashing the SD Card with the software.
However if the Unit is new or still under guarantee, I am sure that Paul from Brennan (the moderator/owner of this Forum) will pick up on this thread and make suggestions to help sort you out.
If your machine is out of warranty (12 months I think) then if you come back to us we will "talk" you through what to do next (short of sending it off for repair).
Fred