I did it last year, going back to do it again, leaving on monday evening, yippee!
The course is technically challenging - as you say, you've got a tricky quarter side-on sea out to the Nine Pins, a nice downwind to the Kissing Whales aka Cape D'Aguilar, then a side chop/headwind back to the finish at Stanley. (Usually!)
Last year, I'm told, was a particularly mild year. I still found the section out to Nine Pins challenging - I was on a V10 Ultra, which I'm not used to and which I found a little too lively for me. I battled to catch the diagonal runs. On the long leg down to the Kissing Whales I had a ball and caught a bunch of guys and then ground away back to the finish, being overtaken by a V12... I wasn't as fit as I should have been but I wasn't happy with my performance!
The water around the Kissing Whales is a maelstrom of reflected waves forming klapotis with the oncoming chop, so you probably want to go out there a couple of times from Stanley during the week before the race if you can. I'll be doing it Wed, Thu, Fri probably in the mornings.
That's the worst of it I think. If you can survive that, Nine Pins is not as hectic.
But for your first one - if you can get an Eze or V8, you'd probably feel happier! I'm doing it this year on a Think Evo II, a nice stable intermediate boat that I've been paddling this week for the first time!
It's not an easy paddle - it's challenging - just as a World Cup race should be.
Rob
Currently Epic V10 Elite, Epic V10 Double.
Previously: Swordfish S, Evo II, Carbonology Zest, Fenn Swordfish, Epic V10, Fenn Elite, Red7 Surf70 Pro, Epic V10 Sport, Genius Blu, Kayak Centre Zeplin, Fenn Mako6, Custom Kayaks ICON, Brian's Kayaks Molokai, Brian's Kayaks Wedge and several others...