Better yet, buy two (or get a friend to buy one also, which is what I did).
Seriously though. The AI is the most fun I've had on the water in years. It sails you to the places that are too far away to conveniently take the kayak, but will take you into the places that are too tight, shallow, etc, to get into with the sailboat. Like you, I'm a small & large boat sailor for over 30 years. I've sailed Lasers, Sunfishes, Flying Juniors, and numerous other small boats over the years. I also own a Hobie 16, which is also a lot of fun. For the record, the H-16 hasn't gotten wet since I picked up the AI in May, '07. I've had the AI out among the other boats on numerous occasions. I won't sit her and tell you it will outsail every other boat on the bay. Some days the Lasers & Sunnys leave me behind, and other days I leave them behind. I can tell you, without any fear of contradiction, that the AI is a ball to sail. It'll get up and go in the big wind, and the waves. It'll also give you a good sail when the wind is light. And, having the Mirage Drive pedals available as auxiliary power is sure nice too. As for the lack of a boom, yes, that is a bit of a drawback. However, (gotta love the users forums) somebody has already come up with the solution for that. Do a search through the archives for "barber hauler" and you'll see what I'm referring to. Single line that runs from a block hanging on your mainsheet, out to the aft end of one ama, across behind the seat to the aft of the other ama, and back to the block on the mainsheet. Nice, simple, neat design. As one of my engineering professors in college liked to describe such things, "An ELEGANT solution."
You also asked about transport. I tow two AI's on an aluminum Trailex SUT-250 behind my MINI Cooper Convertible. At only 115 pounds each, even a small car like that pulls them without a problem. I can also rack one on top of my Ford Excursion 4x4. I don't do that very often, as I don't have an actual kayak rack for the truck. Foam noodles and cinch straps do the job in a pinch though. If I had the right racking equipment, I could put two AIs up on the truck as well. Loading isn't really a problem. It can be a bit awkward, as the roof of the Excursion is about 6'10" high. Still, the main hull only weighs about 65 pounds, the amas only about 15 each (rough guess), and the rig another 8 pound (again, just an estimate). The hull is the only "heavy" piece, and 65 pounds isn't much. With the right racking equipment, and I'm certain that somebody here is going to reply with that info, cartopping an AI would be a piece of cake.
If you've read any of previous posts, and I highly encourage you to read them all, you'll see that the AI is not without it's growing pains. Hey, the design is less than two year old. But you will also see that Hobie has been paying attention. Note that this is their forum, and they do participate here. When problems have been discovered, solutions are developed.
One other thing I love about the AI is the speed with which I can be "feet wet & sailing". With the H-16, I needed and actual ramp to launch from the trailer, which had to be towed by the Excursion, not the MINI, and rigging took 45-60 minutes. With the AI, no ramp needed, and I'm sailing in 10-15 minutes after I arrive. Can't beat that!
Sorry if I got a little long winded here, but I just can't say enough good things about this boat!
- Jim L