Make sure the drainplugs are in tight. I back the trailer to the water and simply push the boat off the trailer and into the water.
I unload it by myself so two people is a breeze.
I really haven't had to use the oar. Assuming that wind is blowing on shore. Unfurl the jib so that you don't weather into irons. Mainsheet loose. Jump on the back as you push the boat out. Drop the rudder, unlocked, into the water so you can steer it somewhat. Tighten mainsheet and accelerate. Once you're in deeper water, lock both rudders, adjust sails, get favorite beverage out of cooler.