A most interesting design I saw in a book was where you were essentially sailing a wheelbarrow. The boat was about 10", standard/classic rowboat/sailing dingy lines. The bow incorporated an epoxy covered foam sheet wheel that was recessed into a pocket in the bow, protruding just enough for the wheelbarrow/boat to roll on it. At the stern, the gunnel stringers extended beyond the transom for about one foot, ending in a classic handle shape. You wheelbarrowed the boat out into the water, and stepped on. Very slick!

Now, you could incorporate that idea into a kayak, particularly at the stern. Designing a slotted tail with a recessed wheel that sat in it. Shouldn't affect performance much, would still allow the use of a rudder or skeg if desired, and would be a handy rolling point, with you holding the bow loop.