In comparison to windsurfing, kiteboarding is like cheating and gambling.
It's like cheating because:
1. You can plane in light wind without a big board, heavy rig and arduous sail pumping.
2. You can jump high and do a variety of easy tricks and transitions without strong wind, waves or expert skills.
3. You can ride in shallow or weedy water without worrying about your fin catching.
4. You can get out through breaking waves relatively easily.
But it's like gambling because:
1. You have a greater chance of missing sessions because of gear troubles, e.g. leaky valves and air bladders.
2. You're more likely to get stuck out on the water and less able to get back in on your own.
3. If the wind is too light you can't do ANYTHING, versus with windsurfing where you can at least shlog and stay upwind.
4. Sometimes you can't go even when it's windy because the wind is inconsistent or there isn't a suitable launch site.
5. There's a very good possibility that you'll have an embarrassing, expensive, and / or life-threatening accident.
The Lament for Icarus, Herbert Draper, 1898, a clear enough visual metaphor for the follies of kiteboarding. At least the nymphs dig it.
Anyway, since I started cheating with kiteboarding a year ago I've tried to maximize the benefits and minimize the negatives, with mixed success. Recently I thought that by switching to a wind-inflated "foil kite" I would be able to avoid the durability and heaviness problems of "wax and feathers" inflatable bladder kites. I like how the foil kite flies, and I like not having to pump it up and pray that it holds air, but it still drops out of the sky when the wind falls below about 8 knots, and it's more of a hassle to get back in the air than an inflatable, especially when it gets all wet, tangled with seaweed, sandy, and full of water. Here's a video of me using it in just-barely-rideable conditions. (Notice my new GoPro camera arrived.) The song is by the French band "Air".