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As fanoush mentioned, you definitely can. Being able to reprogram the watch was one of the reasons I bacled the kickstarter, because the watch is opened up to all kinds of firmware without having to sacrifice waterproofness. I've tried it as well (had a female usb connector soldered onto some protoboard and broke out the pins to a j-link adapter)
@fanoush I wonder if the usb/swd cable can be used for installing the DFU and maybe factory reset the watch? Or maybe even run a small diagnostic that gathers data on the watch as well as some data on the responsiveness of the peripherals. Might help with troubleshooting in the future.
Yeah, you can't reprogram it from the charge cable. At least that's what they say.