As a newby kiter for just about a year now I can totally relate to your kiteboard learning experience. While a little older at 51 I too have been a waterman my whole life (sailing, windsurfing, freediving, waterskiing, wakeboarding, wakesurfing, surfing, scuba diving, spearfishing, jetskiing, kayaking, etc…). I also thought kiteboarding looked a lot easier and safer than it is, at least in the beginning stages. I also thought I would be able to progress much faster than I have, probably due to the fact that I’ve been able to pick up other watersports rather quickly. I did the Progression and other DVDs as well as YouTube videos, trainer kites, flying full size kites in parks, etc… I agree that a lesson or two is a must for first-time kiters.
However, my experience has been that practice time on the water, whenever possible with other kiters you know and preferably at a familiar launch with winds favorable for beginners, is the best way to proceed after an initial lesson or two. My only problem with lots of lessons without enough practice time spaced in between is that this sport has such a steep learning curve that some new kiters can end up wasting a lot of money on additional lessons if their kiting skills don’t really qualify them for their next progression/lesson. This is mostly our own fault because we try to ‘hurry’ our own learning. This is particularly true of people who try to learn to kiteboard/surf while on a vacation. This situation can be compounded by the fact that kiteboarding instruction is a business and instructors are there to make a living. I’m not dising kiteboard instructors at all. Their awesome and I love them, but what I’m talking about is a balanced learning approach.
My experience has been that many schools and instructors will push for “more lessons” even when they know what you really need is time to practice and master what you’ve already been taught. For example, how many people can really self-rescue properly or have the wherewithal to pull their QR during the initial stages of a kitemare after 8 hours of back to back lessons? Not many. Yet many can get up and ride at that point. I’ve learned that kiting safely is so much more than getting up and riding.
What I found worked best for me was some initial instruction followed by lots of practice time with friends at my local kiteboarding spot. I also bring a waverunner for rescue purposes if things go really bad (I kite in the Gorge). After wasting money on a lesson that I didn’t get much out of (through no fault of the instructor) I’ve since learned when a lesson is what I need vs practice.
Flame me if you will but I now ride a lot better and safer than others I've seen with many more lessons under their belt.