I haven't moved one quite as large as that, but close. First, don't get in a big hurry, you will make mistakes that can hurt!
As far as tipping it up on edge, be careful, use 1/8 or 1/4 inch steel shim plates to make it go up a little at a time on each side. Don't try to put a 2x4 under it until you have the other side up near to that height.
I used steel pipe to roll my safes on, rather than golf balls. I carried a bunch of them, and would feed them under then front as it moved forward and they dropped out the back side. Not sure how strong your ramps and dovetail are, but steel beams laid over the ramps and extending past the dovetail will help spread the load. Use 3 or 4 or more and it will really help spread the load. Pipes will roll right up the beams and as the load nears the top of the ramps, the beams tips will lower down to the bed of the trailer. Pipes rolling rather than greased boards or steel will work better in my opinion.
I have a 6 ton comealong, that I use to pull heavy things. Worth it's weight in gold, big pain in the rear, but will never do without it! (chain style, multi pulley). The only duty cycle it has is how long my arm can stand cranking it! I picked up a cannon ball safe with it and sat it in the back of my pickup. As the feet reached the bed, they crushed the steel bed making imprints of 2.5x2.5 inches for each of the four. Didn't drop it, just kept letting it down, and it kept sinking. Dang thing was heavy also!
Rollback of the automobile style won't handle it, they typically max out around 8k. A larger one should be able to handle it, just make sure they know a typical rollback is not enough. A semi truck wrecker should have no problem lifting it and setting it on your trailer, but what are you going to do with it then? You will have to make sure he follows you home to unload! I think i would do the larger rollback way if you can find one or as was suggested, a machinery moving company. Both command higher rates but if you set up the time to their schedule, you should be able to negotiate a better rate.
David from jax