Well, since my dad has a sailing boat, with a very very nice trailer to stick it on (which is hardly used since the boat is on a mooring) I have kindoff stolen the trailer for my little boat
It's a dutch design i believe, and its called "Freewheel" (the trailer is from The Netherlands)
My dad is probably going to kill me for saying this, as he is scared of everything getting stolen once it is on internet "advertised" that we have it..
The trailer has a pin which holds the drawbar to the whole frame, once the pin is pulled the whole frame swings up, rotates at the axle and makes a ramp (IDEAL for launching over the edge of piers) also, the tyres NEVER have to get wet due to the design. and there is no need to haul the boat up the Bl**** trailer, as it has a winch which will pull the bow up onto the first two rollers, and the whole frame will balance the boat and slowly come back level onto the back of the drawbar, where the pin will click back in, and you are done.. At the moment the trailer is set up for our sailing boat, but it can be fully adjusted...
As for the outboard, if the distance is less than 5 miles i just leave the outboard up and on the back of the transom, but as soon as i go any further, i remove the outboard (due to the weight on the transom of the outboard bouncing up and down on these roads..)
as for the buggy idea... this boat should have a buggy with it, but my brother forgot to bring it along.... REALLY usefull.
However, the boat floats in about 10 inches of water, so it is not hard getting out and pulling it the last hundred metres up to the shore, and then pull it ashore..