Anstigmat wrote:...I've rigged up a way to sort of lift it off the trailer using two very heavy duty ratchet straps.
I once rigged a garage with two loops of rope. Each ran as an endless loop through a block. Well, not truly endless, because of the knot that formed the loop.
The blocks were attache to some purchase I rigged up. You can get the ready-made versions from the hardware store, they're cheap but OK. I made mine from real sailing blocks (expensive). I added a cascade so I could get 8:1 or something like that.
I sling the ropes around the boat. Lift with the purchase, belay the free end, and then, with the boat in the air, I can "flip" it by rotating inside the endless loops (the loop turns with the boat and runs through the block as you do that, so make sure the knot is on the correct side when you start).
Obviously, I did the turning very close to the ground, why challenge fate: but I did not need a helper with that setup to get the boat off the trailer and on its side inside the garage.
So, yes, there's millions of ways to do this, none are truly hard, and with a bit of smarts, you can work out how to do it alone. Or get a few buddies. The DS is heavy, but not too heavy. But I've careened an O'Day Mariner to do a CB repair underway. We were four, but mainly because we needed to have people on both sides of the hull for the repair.