Ha ha 1999 hey, I was wondering what sort of vintage the sky pirate was.
I just did the L2L on a 7'6" Naish Sky Pirate (with a different set of fins in) it didn't go to bad until I hit a few big clumps of weed a couple of k's from home and lost a heap of spots, ended up coming in 19th with a time of 28:17.
I was able to jump/pop over a few clumps of weed early in the race but towards the end it was getting hard to lift the 7'6" lump of lead weight with my legs burning and on my non prefered tack.
When I hit the big clumps they caused so much drag I just about stopped and had to send the kite to get the thing airborne a few times to clear it.
I can't imagine jumping the beast just for fun.