Since debugging USB devices is a common use case (I've certainly done it innumerable times), it is imo reasonable to have workarounds in OpenOCD and other debug tools to ensure this use case actually works reliably. Whether or not moving the two devices to separate USB controllers works (and it's a good idea to try!), that option won't necessarily be available to all users (eg debugging with a laptop that has only 1 USB controller). Making the timeout a configuration is an option, but is that really...