I'm an independent personality unable to acquiesce to not being able to do it myselfAsk for help from a couple of people
What about replacing the trailer tongue with something like above? Pull a pin out. Slide tongue out several feet. Latch again and you have the tongue extended. Slide it back in when you are ready to tow home.Some of the private ramps along the river here in Parker are pretty shallow. To get small boat and PWC trailers deep enough, lots of people fab up two-wheel dollies like those used to tow aircraft. One guy actually made his from one of those actual aircraft dollies.
With an extra 10-15 feet of length you should have no problem getting the trailer deep enough to float off/on.
At the top of the ramp with the wheels chocked, remove the dolly, hook up the trailer as normal for highway use.
Here’s an example from Google
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