Might try cutting the aluminum plate down some to give you some more room up front, especially on the right side/opposite side of the TM mounting spot. I fish solo and am 70 y/o. I have a raised platform where my TM mounts, and I can get on my knees to hook the bow winch line up after loading on the trailer. I also can then crawl down and put one foot, then both feet on the trailer tongue to tighten down the winch strap. I then have to usually jump off the trailer tongue over to the edge of my truck to get in the truck. I could wear rubber boots but haven't so far to avoid wet feet.

Other option I see is to back the trailer in a bit deep, then using a long rope, just pull/float the boat onto the trailer. Wear rubber boots as needed.