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Some pipes to roll it along will help as well.

That is thinking outside the box. 3 ea 2x8 as a ramp would work as well, pull it up the ramp with the come-along. They would have to be long enough to prevent the generator dragging at the back side and most likely need some support under the 2X8 to help support the load when it is pulled up.

Long 4x4 that are longer than the trailer is wide enough to clear the wheels. Just keep jacking it up put concrete block on each side and when high enough back the trailer under it and lower it down until you can rest on the concrete blocks on the trailer remove the long 4x4. I think raise it...

A low cost come-along, $20 or so, would hook to the front and then use it to pull the generator forward on the pipes. If you back your vehicle up onto some wood blocks this would raise the front of the trailer some and lower the back.

I unloaded my MEP 03 engines with a pallet jack using this method in reverse. Yes the engines only weighed about 600 lbs each. but it worked metal pipes helped roll it and make it easier. You could try what I call cribbing. Use the pallet jack to lift as high as you can. Put 4x4's (pallets)...