Interesting timing on this thread. My wife and I are getting our R27 prepared for a 2 week trip the end of the month, and we wanted to bring the kayaks. I mounted kayak holders on the roof rack, then we brought one of the kayaks down to the dock to practice loading and unloading. We quickly realized we couldn't lift the kayak from the side while balancing on that little lip, and the stern was out of the question due to the canvas. We could get it on there by lifting it up from the bow, putting one end on the roof, then sliding it back into place. But this involved a great deal of rubbing and bumping, including a couple of those skylites, and we felt quite certain that we'd damage things if we did this regularly. In the end we decided not to bring the kayaks this trip. We chose to remove the kayak racks, as I certainly don't want charterers attempting that.
At another marina last summer we spoke to a couple with an R27 who created this fantastic kayak loading system. It involved swing-out bars on the rack with pulley systems. They'd swing the bars over the side, hook the lines on the kayak, hoist the kayak tight to the bars with the lines/pulleys, then swing the bars up and over placing the kayak upside down on the rack. When I have some time, I may consider building such a contraption for our R27.
By the way, if any of you Tugnutters happen to be that couple we spoke to, please post pics of your marvelous contraption you rigged up!