As I understand you want to pick the boat up by the bow, let it hang vertically to clear the gunnal, and stand on its transom in the cockpit for transport. The davit it's self can be extended by as much as another pipe section (about 4 feet), and you probably could clear the gunnal. But I would be concerned by the mounting position. I have used a 12" extended standard with a bumper hitch, which only support is a pipe running about 18" into the lower pipe section of the davit--and that worked fine, to pick up 80# of a rolled up air floor dinghy onto the back of a truck.
Looking at your photos, I believe you could get the bow up high enough that you could grab a corner of the transom, and lift that over the gunnel, without stressing the height of the davit. Even if you had to boost 2 feet over the gunnel, that would work. There are many advantages of a small skiff as a dinghy. My dad made out of plywood in the 1930's and it was still going strong when we sold his last sailboat in 1980'--so you might call it a "50 year" dinghy. He did not use fiberglass, but copper glued and nailed on the chines to protect the edge of the flat bottom plywood. No thwarts, just a center hollow 2" center floorboard, which all passangers sat on--tangled legs were the norm, but the rower had first choice of position, so the rower was properly braced. I don't know the exact weight, but I suspect is was in the mid 40 lb range. Also it had an inner chine and clamp, no keel, and a little rocker. Easily carried over one's head and back, by hands up and holding a rib about 2 feet back from the bow.