Well,--let me answer your question by telling you why I take my boat off my trailer. It's easier to sand and clean the bottom, get at the centerboard to check the shackle and pin, and also to bottom paint the whole hull. In short, it's just easier to work on the hull without having to climb around and over the trailer.
How do I get the boat off the trailer? I lighten the boat up by taking everything out of the cabin as well as removing everything else like the outboard, rudder, mast and Etc. Then I use four of my Brownell SB-3 sailboat stands on the stern to lift it, plus a hydraulic jack and a straight powerboat stand under the bow close to the keel. I keep the boat level as I raise it up off the trailer and I shore up under the stern with 6"x6" wood blocks. It's just a matter of jacking the bow up and moving the trailer ahead with the straight stand attaining the height. I may move the trailer about 15" or 20" ahead and have to jack up the bow and move the straight stand ahead or on the other side of the trailer's cross member.
Once the keel is clear of the last cross member, I raise the bow up a little and shore up under the keel with blocks and take the trailer out the rest of the way. One sailboat stand from each side is then moved forward to the appropriate area of the hull and she's good to go.
I don't advocate that everyone try this because it is dangerous.
Also, boat stands aren't made to lift boats as you well know.
With that said though; my sailboat stands can lift my O'Day 222. I also used my boat stands one day to lift my friend Ray's 86 O'Day 26 off his trailer and it was fully loaded.
He pulled it out of the water that night and the boat was sitting crooked on his trailer with the keel off the keel board a couple of inches. The tide went down and it was too late to back down again and straighten out the boat. To tell you the truth, I had more of a problem trying to slide his tandem trailer sideways than I did to lift his boat. I didn't think of it at the time, but I could have jacked up his trailer with my Speedy Lift hydraulic jack and let the wheels of the jack roll the trailer sideways. I just discovered this trick about two years ago and it works. All you need to do is pull it over with a block and tackle from a tree or something that won't move. If you had to do this on the ground, a short plank under the jack will work for the wheels to roll on.
So that's why and how I do it. I know that Ray learned quite a bit about lifting his boat that day because he needed to remove his centerboard and was able to do it himself at his house. Although, he told me that he didn't take his 26 completely off his trailer, but he got it off far enough so that he could remove the centerboard.
My other friend Jeff used a backhoe from the farm where he worked at, to hold the bow of his O'Day 25, in order to get it off the trailer. He had a pit dug under the keel so that he could drop the centerboard down to get at it.
I talked to a guy who used a long metal eye beam to hold the bow of his O'Day 25 in order to set up his tandem trailer.
This whole operation is even easier with a roller trailer. You just rope off the stern to something solid and pull the trailer out from under the boat, shoring up as your go along. Like I said though, --it's dangerous. You really need to think it out and take your time. Take every precaution to make sure that you shore up under the hull just in case something goes wrong, the boat won't fall far, tip sideways, or pitch-pole forward or backward. Email me and I'll send you some pics.
sailtrinkka1986@verizon.net
Joe