My
Boler has a 16" top-of-frame and top-to-ball height, which I'm guessing is at least as high as a
Surfside. My tug is a Sienna, with a lower floor than a Highlander, and a taller hatch, both of which suggest to me that the bottom of the hatch would swing lower than that of a Highlander. My jack is mounted through the hole in the back of the coupler, as far forward as possible. The trailer rides level.
The net result is that I should have hatch-to-jack clearance problems, and indeed I must have the handle of my front-wind jack in the down position to clear.... but it clears. I would be surprised if it's necessary to go to the trouble of changing the jack mounting to clear the Highlander's hatch.
If the rear of the tow vehicle is pushed down too much by the tongue
weight, that will increase hatch-to-jack clearance problems. I use air bags in the van's rear suspension, which essentially eliminates this potential problem.
My jack is presumably the 1979 original, and other than the plastic of the handle grip coming apart (not completely yet) and the foot being missing (it's just a tube end now, distorted by being dragged at some point by a previous owner) it is working fine. I believe that it's an Atwood, like the coupler.