hey mate, it all depends on how old the boat is and if the trailer is a good one. Generally a boat over 16 feet long is a 2 person job. One to hold a bow rope and a stern rope from the jetty (if there is one) and one to let off the winch at the front.
when you are retreiving it, keep the person on the jetty with the bow and stern rope (this is usually one long piece of rope hooked to both) and push the boat away from the jetty so that the boat lines up, if they push too far, then get them to pull the lines till it is in line. then hook on the winch and wind away.
Its easier if you unwind your winch before you back the trailer into the water and put the hook on one of the back pulleys, out of the way of the wheels.
Good Luck,
Az