Hey Joe,
I'm not sure but I reckon it would have been around 1998 or early 1999. The last time I was in Maui windsurfing was in 1999 and a few guys were riding Wipika classics like in the video, they were just staying upwind and were riding at Sprecks. I'd say that puts the video at around mid 98.
Tis good to go trippin down memory lane eh?
The good old days! When you could only buy two kinds of kite, either Naish or Wipika, both were two line and low aspect. A massive kite was an 11m, anything bigger hadn't been invented and was ludicrous to think you would need more power than an 11.

Stonker was the only board manufacturer in Australia to my knowledge, and was selling polyester 195 directional with 5 FCS fins. Three straps and you had to gybe them.

Twin tips hadn't been invented at that stage. Kites inverting never happened, luffing was common, edging was essential. You got worked in big gusts.
Safety releases were absolutely primitive and often didn't work. Pumps were the small hand held jobs and made you look like you were "spankin' the monkey" every time you pumped the leading edge.

Valves in struts and leading edges were the type that had to be squeezed to release air all the way until they were flat and the neck was only about 6mm in diameter, even on the leading edge.

We used harness lines with no safety releases. No one knew how to ride upwind to get back to your board so we all wore surfboard leg leashes. We all wore wrist leashes.
There was no crowding problems, in fact, if you saw another kiter, they were like a kindred spirit and you became instant friends. We worked on hard tricks like toeside riding, jumping and back rolls. Table top jumps were all the go and a groovy little move called the "candle stick".

I miss the days with all my old pioneering buddies, the sport was so innocent and everyone was supportive. There was no bitching or quarreling, there was no attitude. Everyone was pushing new boundaries and open to new ideas. The sport was an oddity and would stop traffic. It always drew a crowd, even just riding back and forth.
Good times!
Good winds,