Re: When's the sale?
The best way to get a deal is to check out the different wakeboard sales sites, and click on the "Closout" deals.
If you're okay with having LAST YEAR'S graphics on your board, you can generally get the board for HALF what it would have cost last year.
I got my wife the Hyperlite Syn for $170, despite a $380 MSRP. Due to it being a 2007 model, instead of '08. Of course, the graphics were MUCH more to my wife's liking than this years' anyway, so it was a win/win situation.
I did something similar with my snowboard a couple of years ago. A $520 board for $160. All because it was "last year's" model.

Some people will pay 2-3 times more, just to be able to say it's THIS YEAR'S model. For one year, and then what?
Talk about having more dollars than sense!
I guess it's a good thing for me, that so many other people are so stupid...