Ive done it, the lights dont shine back 75 ft though so it becomes a rather spiritual experience not being able to see the wake.
Last year at midwestwakefest we went out at 3 am and I still drunkenly managed to pull a backroll and bs 180.....still to date one of the coolest things I have ever done.
I can only offer two tips, use "glo sticks" on your lifejacket so the drive can find you, additionally, bring a 1,000,000 candlepower spotlight along for finding riders, aiding vision, and MOST IMPORTANTLY, shining ahead for the driver.
www.midwestwakeboarder.com