hey all - long time reader, first time poster ;)
Kiting with waterskis was tried right from the very beginning. There's a pretty decent documentary called
'UPWIND - Launch of a Sport - History of Kitesurfing' which features some of the pioneers of the sport and which shows this. Here's a segment where Cory Reeseler (I think) is jump launching a two (!) line kite off the rocks onto the water wearing waterskis off Maui. Not a lot of safety in those days...
(if the link doesn't work it's 3:40 in)
The doco is worth a watch if you've got an hour spare with some interesting stuff on how the kite and bar tech evolved in the early years.