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Here are a few thoughts.

I too had a LoadRite trailer like yours, they are great. The hull sits inside the wheels. Check my project album.

While this sounds a bit cowboy, I am a veteran in transporting cargo, people and supplies from the mainland to islands with no ferry service. I used my boat 9 months a year (ice and snow) and in nasty weather.

I would replace all the rollers and brackets. I would set the keel rollers down lower to drop the boat as close to the frame of the trailer as possible. New bunk brackets are also required. The existing are too long and need to be cut off. My Outrage 17 was really low to the ground, the engine was trimmed way out so not to scrape the ground.

I re-read Chuck's description of the ramp and tide conditions.

Here is my take to launch at that ramp at 0 tide will take a longer tongue. Since maneuvering at the top of the ramp is hard, I would start with the swing out tongue kit from Fulton. It adds 3' and is bolt on. Easy to do.

IF not enough, I would replace the tongue jack with a 2- wheel type to the bow frame of the trailer and add a second jack on the opposite side. This supports the front of the trailer allows it to be de-coupled from the truck and moved around.

I would add a second 2 speed hand winch to the front of trailer post or top of the tongue and use it to attach to the truck.

Back the trailer down the ramp as far as practical. Place tow vehicle in park, then hook up the second winch to truck, decouple the tongue and unwind the winch to dunk trailer. Once the boat is off, re-winch and reattach to the truck and go.