A warm welcome from the AI Community DownUnder.
Re trailering vs cartopping, I would check out the various options deliberated regularly on this site before commiting. I for one am an enthusiastic car-topper and have no trouble getting the AI on and off one-up, and would recommend going that way though there are many from the other camp.
Again check out the various carrier options through this site. The balloon wheeled Hobie cart is an excellent choice which I believe would allow you to wheel your AI in under the house backwards with very little trouble. I have even third filled my balloon wheels with water giving them greater stability over rough ground as well as less buoyancy, an advantage for ease of inserting them into the scuppers whilst in the water. Why re-invent the wheel if you don't have to. Good luck....Pirate