There may be another problem. It may be just the photo angles, but it appears that the crane’s blocks are not positioned directly over the outboard. So when the OB is lifted from the dinghy transom and raised to the height of the rail, the OB will not be directly over the mounting pads on the rail, etc. It will have to be manually pulled over some toward the boat’s center. Not as easy as it should be, especially if the boat is moving. Rocking, for instance. You’d have to ease the fall in which case the heavy weight (OB) will pull away from you. A difficult “one-arm lift” where it is not easy to get leverage over.
As somebody who has done countless OB engine lifts from the dink to a stern rail, and vice-versa, it’s a process that requires balance, timing, and some degree of leverage. I’ve come to the conclusion that the dink should be firmly tied to the boat with the transom directly below the crane, so if you must push against the load as in stabilizing a swing for example, the dink does not scoot out from under you. It’s best if it’s a short, straight-up vertical lift from the transom to the rail mount. This is best done at the quarter, not directly astern. Attempting to hoist at the stern to an outboard “seat rail” from an offset crane a bit too far away will not work out well in my estimation, considering the OB weight. For one thing, the crane will want to swing outboard. It may be too long. The lifting crane should be short, inboard, with the blocks positioned directly over the load when lifting, if possible. (Curved stern rails make it hard to securely attach the rail mounting pad exactly where it should be.) Otherwise, the crew has to “manhandle” the OB onto the pad, as well as off of it.
Before you spend boo-coo bucks stabilizing the mount, if you do, I advise you to take the boat out and anchor it; say in Vinoy Basin there, and try out mounting and recovering the outboard with the set up you have in place to see what you’re up against. Next imagine lumpy seas and strong wind veering the boat all around while you and Mrs PP are struggling to get the OB up to get under way. It’s just not that easy. Next, you have to get the 10 ft dink aboard or be ready to tow, etc. Of course, if you decide to tow with the OB still attached, then that would be quicker.
Unfortunately, swapping a 15 hp for a only slightly less heavy 9.9 hp doesn’t really help that much with problems I describe the re:mounting & recovering. In the end, an OB that you can lift and handle (with facility) with one arm is best. Even the 5 hp four-strokes are heavy, 40 to 50#s. I’ve muscled one of those SOBs around for about 20 yr now. I have a virtually new Honda 8 hp with about 20 hr on it sitting out back on an outboard dolly (yeah, had to buy one of those to get the OB from the car to the boat!) since May. I put the “lighter” 5 hp Tohatsu on for my trip up the coast in June. Just took it off Sunday for servicing. So, regarding above, we’d be talking 30#’s or so, which is in the 2.5 hp to 3.5 hp range for four strokes. But then, problems solved, etc.