I will second what Bill said regarding how to rig the boat. I can do it in 50 minutes alone, 35 with some help. I am 39 but no strong-man, but nothing I do requires a lot of strength. Some things I do: a) I keep the shrouds and backstay connected, don't touch them. The previous owner must have ground the base of the mast, as it goes up easily this way. b) I had a local shop here set up a vertical steel bar that extends the winch support on the trailer, and goes about 1 foot above the front pulpit, and I had them weld an eye there. What I do is I attach one end of my main sheet to the eye and one end to the forestay, after the mast base has been positioned in the tabernacle and the bolt was put in (but the nut is still somewhat loose). Using the 3-1 purchase of the forestay makes it relatively easy to raise the mast: I raise the mast by pulling up on the forestay a bit, then tighthen with the main sheet; repeat. After it's gone up to about 30 degrees you can just pull it up easily with the main sheet. What's nice about the system is that I am all the time at the bow of the boat, so when the mast is straight all I have to do is connect the forestay. (Also, even if something terrible went wrong and the mast came crashing down, it wouldn't hit anyone.) The only thing I have to be careful with is making sure the metal triangle in the backstay comes up the right way, which is achieved by lowering the backstay to the ground, behind the boat, before raising the mast. c) I never used the trailer tongue extension. In fact I sold it, it was way too heavy and I would never have been able to rig it alone. With my 3.5L Honda Odyssey I have no problem launching at all the ramps I ever go to. d) As Bill said, you have to have a good plan on the order in which you do things. First time I rigged it also took me 2.5 hours (and when lowering the mast I managed to drop it!! Luckily no one was harmed.) The biggest saving for me was installing the mast-raising system described above and using it well, and finding a set system of using ball bungees for packing the shrouds. Right now I walk around the boat and do most things I can do once, then hop in the boat and raise the mast, rig the boom, and get the sails on, throw out of the boat the bumpers, dock lines, and the bronze bar supporting the rudder, get out of the boat and install the rudder, bumpers, bow lines and I am ready to launch. With a boat cover (from Sailor's Tailor) which takes about 5 mins. to take down and 10 to put up, I count on about 45min. - 1 hour to rig, and about 1:30 to derig and put the boat away. For me that's still a lot, (I trailer sail, so rig and derig each time I go sailing) but it's surely better than what you have. Andrei.