I used to trailor sail a Jaguar 22 [ Catalina 22 clone ] and could raise the mast by myself. Ok was a bit wobbly at 45 degrees but made it every time OK. Used the spi pole as a gin pole.
Just be a real carefull about power lines though. A cruiser was killed in Trinidad recently when his mizzen hit a line during a drop.
Can't help with the ramp though.