Taking a boat off the trailer
Jake,
I first started taking my old 19' wooden Thompson cabin cruiser off it's roller trailer back in 1974. I'd raise the 80HP engine off it first with block & tackle, and store it on a stand in my garage. Through the many years I had been doing this, I had some idea of what was needed to make the task safe and easy when I first started removing my new 1986 O'Day 222 from it's roller trailer. As Buck points out, it is very dangerous. I no longer have a roller trailer and the job is a little slower and involves a hydraulic jack, 6X6"X 4' wood blocks, plus 4 tilted SB-3 Brownell's boat stands and one straight powerboat stand. I'm not going say that a guy who works in an office should not even think about doing something like this, because I've worked in an office myself, but I also did line-work for a power company for 32 years. So rigging, and lifting heavy weights with machinery are nothing new to me. With that said;-- unless you know someone who has some knowledge of doing this who can help you, you would be better off having the boatyard take it off and the trailer and put it on stands until you get your trailer back into shape.
Joe