John, Buy the boat! We'll help with the rest.
We have a 95 H26 with the Hunter trailer. The boat trailers like a dream with a 3/4 ton pichup. A 1/2 ton truck is a bit of work.The boat comes with the mast raising short shrouds, and that, with the main sheet/block assembly is all you need to raise the mast. If the boat doesn't have this then call Hunter and get the shrouds. (it's got to be less that $100). My wife and I pull into the launch ramp and within 1 hour we will have raised the mast, rigged all sails, loaded the coolers and gear and launched the boat.We leave our boat in a slip that has about 10 feet of water. We leave her with the keel and rudder down.The boat doesn't steer very well with the rudder up. Actually, unless the rudder is FULLY down the boat doesn't steer worth a darn. We dock or leave by moving slowly and taking the OB in and out of gear and steering with the rudder. Since we don't have remote controls for the OB my wife runs it and I steer. Works well as long as you share the blame.The Hunter 26 is the best boat, for a reasonable cost, a person could buy. It will gracefully teach you to sail, and will stomp anything in the neighborhood when you can sail, while allowing you to enjoy a very comfortable live aboard lifestyle.We are retired and sail our boat 3 to 5 days a week, every week from June to October and live aboard. We anchor or beach every night. We raise the centerboard and rudder and then stop about 100 feet off shore, drop the anchor, and back into the shore with the OB. About 15 feet from shore we shut down the OB, raise it, and beach. Run out an aft line and enjoy your nighty walk on the beach.Ray