USB 3 spec says 16 ft is the maximum without a repeater, and the Odyssey has 12 ft cables… so 3 foot (15 total) ones generally work, most 6 (18) ft work, but once you hit 10 (22) un-powered, they generally fail.
The interesting thing will be that USB-powered repeater may work, as it’ll be 15 ft, repeater, then 12 ft of odyssey cable, but it also may draw too much power to allow the headset to function well. Good reviews on the one I bought though, people use it with the rift and the rift sensors. Getting the USB-powered repeaters is both much cheaper, and more convenient (no need to have another outlet, transformer, 5v line to the box) than a fully powered USB extender. When it comes to USB powered hubs, they’re also hit or miss. I have a really nice 10 port powered Anker 3.0 hub, but WMR dislikes it greatly for some reason.