Where in upstate NY are you? If you have a tractor with FEL or a 3PH with some sort of forks, all you need is that, cribbing and your trailer.. I wouldn't bother with skidding it if your neighbor is concerned about his lawn..
I've moved a 12X20 shed (wood-tex brand) about 5 miles (on a sunday afternoon on back roads)
and a 10X12 shed from rochester NY to my farm, I actually jumped through all the hoops to get an oversized load permit.. What a joke that was.
I loaded the 10X12 with just a couple 5' steel bars, a highlift jack and some cribbing.. The 12X20 I just used 2 forklifts, one on each side, lifted it up, backed the trailer under, and was off.. To get it off the trailer I just put some steel pipes between the trailer and the shed skids, and in one case I pulled the shed off the trailer, and in the other I chained the shed to a tree and drove the trailer out from under it..
Though I should point out our trailer is a 20' deckover with full width ramps... Either way it isn't that difficult to accomplish...
Jonathan