Good question! I would like to know as well, maybe as I'm unloading it from the car and it's at an angle on the side bar I could put them on and then lower the rest of the yak off the car so it rests on the wheels. Maybe some sort of strap to keep them on the hull until it gets on the ground, then just take them out while in the water or near water. It all seems like a pain when by yourself.
Maybe improvise some sort of wheel stand so the scupper plugs stick straight up and you just position the AI over the scupper plugs and slowly lower it down. Then just remove the stand. I kind of like that idea...
Yes, it's easy to insert the rods into the scuppers while the boat is up on the side bar then just lift the stern of the boat down with one hand holding the trolley. That's assuming you have lowered the bow first and the boat is upright.
If the boat is already on the ground, just roll it onto its side, insert the trolley and roll it back up onto the wheels, while holding the trolley in place. The trolley seems to be strong enough to handle it.
Addendum: I am using the Hobie cart with standard wheels. I don't know if this works using the beach wheels.