Rule of thumb on Cameras is to get a decent camera body, and sink your money into a nice lens. Everyone will try to push megapixels, self cleaning sensors, live-view, video, yadda yadda yadda. The truth is, without a nice lens, none of that stuff means anything: you'll have a terrible time getting a sharp picture. For your first DSLR, I would recommend buying refurbished. Adorama or B&H are great companies online, I have dealt with both with ZERO issues. This way, you get the most for your money, and aren't paying for the "latest and greatest." Anything around 8MP is perfect.
If you are looking to spend $1000, here is what I would go with. Honestly, it doesn't matter Canon or Nikon, so just get what you can find a deal on. I would recommend a Canon 30D or Nikon D200. Some people will recommend the Rebel XS series (or equivilent Nikon starter camera) because they will take the "same" pictures, but the truth is, you want to have a full featured camera, and the Rebel line just doesn't cut it. They are too flimsy (plastic casing), and will slow your progress because most everything is done through an LCD, and they lack a good focus system. If you aren't convinced, google it. Spot metering is worth the extra money.
For lenses, it depends on what you want to shoot. If you are doing closeup portrait stuff, it's all about prime (aka fixed) lenses. These will give you the sharpest image possible for the lowest price. They also make learning the basics (shutter, aperture, ISO) easier, because you aren't dealing with a variable Fstop at different zooms. I bought the 50mm f1.8 Mark II, and at $90, you can't beat it. Example shot below. Just don't drop it haha.
For wakeboarding, a lens such as the 70-200f2.8 is king. It's expensive, but I've seen them go for 800 or so. Just make sure you get the 2.8 and not the 4...you'll regret it long term otherwise. Not sure on Nikon equiv here...I shoot Canon.
If you have ANY questions, feel free to call, I would be happy to let you demo my setup to see what you think!