My suggestion would be to try before you buy as much as possible. If there are any kiteshops in your area see if they have any demo gear. Also look to the locals and see what they have to say. If you have a local dealer that sells a particular brand it might be best to go with that brand as you can get local service from the dealer if there is an issue.
There are so many different kites and boards on the market it is difficult to say what kite/board combo is the best for you. I have only been kiting for 3 years and have already changed quivers 3 times. This is due to my change in riding styles. When I first started I wanted to ride old-school, then freestyle, and now I just want to free ride and surf waves. This had lead me to my current kit which has kites that are good for riding waves and boards that work well in waves.
When you are starting out it is very difficult to say what your style will be next year or the year after that. I would go for al all-around kite that does everything well unless you are sure you want to go one way or the other, i.e. only freestyle or only waves.
You local conditions will also play a big part in what type of gear you need, which is why I suggested you get up with the locals and find out what they ride. If you area has a lot of flat water and no waves then you might not want a wave specific kite and a surf board and vise versa.
Finally I would recommend buying used gear, but only if you can see it in advance. Back to the local kite shop suggestion, many shops sell last years models or demo gear at reduced prices. You can save a lot of money and will not be out too much if you decide to change kites in 6 months. Right now most kite companies are getting ready to release 09 models so 08 gear is getting cheaper and 07 gear is really cheap. I would not go any later than 07.
Good luck.
mv
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