Right on, KW. Sounds like the Naish boys gave you sound advice. I knew they would. Kudos to you for taking lessons to get started, too. You're on a good track!
Are you already a member of the Hawaii Kiteboarding Association? With the level headed way you're approaching the sport, you might be interested in checking them out if you haven't already. I'm sure you're well aware of the sensitive public relations for kiteboarders at Kailua. The HKA almost certainly saved this beach from being banned already. However, it's a tricky balancing act ovre there and they need all the new members and help they can get to help preserve access and safety. Click here to check 'em out:
Also, you can ask for Noel or Des at the Naish shop. They're both officers in the HKA.
Here's a pic from the HKA site of kiting at Kailua:
The wind conditions in Kailua are somewhat similar to wind conditions here on Kauai. Feel free to communicate with me via private messages (see FAQ) or email if you want to talk. In any case, keep it safe and keep having fun! Nice to meet you~