IK:
A long time ago, we trailered the Dana''s smaller sister, a Flicka. What we came to understand is that the mast and
rigging could be arranged so as to be self-raising/lowering, but that the boat usually had to be craned or lifted into the water from the trailer. The issues were ramp grade and having sufficient depth in the run length of the ramp to enable the boat to be floated off the ramp. In lakes and on the U.S. east coast, this was usually not possible...and that''s IF I''d had the courage to consider doing it, given the tired vehicles we were using.
I can''t see how the Dana situation would be much different...unless you are in a region where the conditions of the ramps is considerably different.
Jack