In answer to your response:
I live on a rather remote island in the Bay of Fundy (BoF); the BoF is renowned for having the highest tides in the world, with average tidal ranges reaching 16 meters (52 feet). This is significantly higher than the global average of only one meter (3.3 feet). The tides are semidiurnal, meaning there are two high and two low tides each day, with roughly six hours and 13 minutes between them.
The local standard for launching sail-boats is to simply back the boat-laden trailer into the water at low tide, wait for enough water to "float" the boat, then launch; for retrieval, the empty trailer is backed into the water at low tide and wait until there's enough water to "land" on the trailer; once manuevered in place, the boat is secured with lines; when the tide retreats, the boat settles and the now-loaded trailer is hauled out.
My initial question was this:
In regards to the Hunter 27, has anyone ever done up formal trailer plans for a similar project?
I closing, you mentioned several regulatory concerns, none of which are a concern here. We have no full-time police presence on our island thus common-sense generally prevails. Google "Deer Island: Suspicious Fire" and you'll see how our community deals with drug dealers.