It’s good to see that you’re doing your research long before you decide to purchase. There are a lot of high quality brands out there that will serve you well. If you’re looking for a good quality and price, there’s Best Kiteboarding.

If saving money is important, consider Best. They make good kites, and they come at very good prices. You can usually get good package deals from them too. The only thing I don’t like about their kites is that there are a lot of tuning options. This means that you have a lot of ways to attach the lines, which can take some time to get tuned in so the kite flies properly. For beginners, it’s more important to just get out and ride, rather than trying to tune a kite.

If you want to spend a little more on a kite setup, I reccommend 100% Naish Kiteboarding. Naish kites are very very high quality, very easy to set up, and they really rock. The Cult is their beginners kite, and it’s very user friendly. The first time I set up a Naish kite, I was absolutely floored - it took much much less time than the Best kites I have used, and I was out on the water within 10 minutes. They also have HUGE depower through the trim line - more than almost every other brand I have seen. Of all the kites I have flown, Naish is my top favorite. Love em!

Other good brands are: Ozone, Cabrinha, F-One, Slingshot…there are a lot of good ones.

The one brand I would be wary of is North. I have seen a lot of people struggle to get North kites set up properly (the lines can be a huge pain). One time I watched an instructor setting up his North Rebel, and it took him 1.5 hours. It was rediculous. Before buying one of these kites, I’d try one out to see if you like it.

Also, it’s a really good idea not to buy your gear until you take your lessons. This way you can use your instructors gear during lessons and save yours the wear and tear. You will also be able to try different kites, boards, and all the other rigging. You’ll get a better sense of what size of kite you’ll need, what size of board you like, and which brand you like (or don’t like). Some schools even give you a good price break on gear.

It’s also a good idea to get an understanding of different kinds of kiteboarding kites, and how they differ from each other. This page has a good explanation, as well as pro’s and cons for each style - http://www.kiteboardingevolution.com/kiteboarding-kite.html

As for online shops, I have had fantastic luck with http://www.kite-line.com . They are a shop out of Oregon, and they have gone through insane lengths to get me gear. I was very happy with their selection and service. They shipped me some gear to Mexico, and helped me work through some customs issues. It was fantastic.

The only other thing that I found really helped when I was first learning was to fly a trainer kite before hand. I flew the kite and mimicked the things I would practice during lessons (plus learned the theory), and it really really helped. If you want to see some exercises you can practice this page has a bunch http://www.kiteboardingevolution.com/trainer-kites.html
References :
http://www.kiteboardingevolution.com
http://www.kite-line.com

Btw, for you, its not kiteboard/kitesurf, you’d definitely be "kiteboarding". Kitesurfing references riding waves, which is several years out for you.
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(845) 294-2078
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If you’re pushing yourself windsurfing, you’re going to find yourself hitting the water at high speeds more frequently than you’d like. Don’t go with Oakleys with a headstrap unless you plan on losing them. I have a pair of goggles that are kind of like shrunken snow goggles that work quite well for windsuring
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Wakeboarding has a good surf feel though, but I guess I’m just wake biased, I’m sure that kiteboarding is pretty cool, but with wakeboarding, you can get out on the water with 3-4 other people and shoot the bull about the great rides until your turn comes up again.

Cable riding and winching are becoming far more popular, and far less expensive than riding behind a boat, more cable parks are springing up around the US every year (and they usually offer passes for almost next to nothing, and there are several winch companys that manufacture some great winches to get a pull from, moreso if you’re into building rails, or jumpin’ gaps.

it really matters as to what you think by trying both of them. good luck in whichever decision you make though.
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I kiteboard and wakeboard, and to be quite honest I love kiteboarding waaay more than wakeboarding. The one that is best for you will totally depend on what you have around you. To wakeboard you’re going to need a boat or a cable park. If you don’t have any of those then you’re screwed.

To kiteboard you’re going to need to learn and have the gear, and you also need the wind to do it. From looking at your username, it looks like you surf - do ya? If you do, then kiteboarding is looking better and better.

Think about it this way - you can use your kite to tow yourself into waves to do some surfing, you can ride on flat water with a twintip (just like wakeboarding), you can launch yourself 50 feet into the air - no kidding - check these pictures:

http://www.kiteboardingevolution.com/Evolutions_Edge-evolutionsedgejanuary2010avrt.html or this one

http://www.kiteboardingevolution.com/Evolutions_Edge-evolutionsedgenovember2009avrt.html

You can kite waves that you would never be able to surf unless you were towed in by a jet ski (or your kite)

You can use your kite on the snow with a snowboard - no lift pass needed, just ride wherever you want. You can even tow yourself up a mountain, pack the kite, and cruise on down.

You can ride sliders, rails, and all sort of other obstacles if you really like wakestyle, but then you can just jump 10, 20, or even 50 feet into the air whenever you want.

Man, you can even kite on land with a landboard if you want.

So between kiteboarding and wakeboarding? Kiteboarding. Catching sick waves, riding to mountain tops, and boosting 50 foot airs sounds much sweeter than paying for boat gas or going in circles on a pond.

I dunno man, you decide.
References :
http://www.kiteboardingevolution.com