Yes, definitely some kind of USB problem.
In VirtualBox high-speed USB is enabled by installing the VIrtualBox Extension Pack and Guest Additions. Those, along with enabling the USB 3.0 (xHCI) Controller are ‘supposed’ to allow you control USB 3.0 devices.
I don’t know where this is going wrong, but I do see that Cypres FX3 device makes the BB60 LED blink red. So it is attempting to connect, but for some reason can’t hold on to it.