Get an engine hoist/shop crane to pick it onto and off of the trailer with, or get a tilt-deck trailer, put the machine on a pallet, tilt the trailer, and winch, come along, or chain hoist the machine (rolling on a pallet jack) up onto the deck and lash it down. If you can't get the machine on a pallet, it can be moved around and dragged onto the trailer with three or even two rollers of 3/4" pipe. I like 3/4" pipe as it's fairly strong, rolls OK, but is not so big the the machine tilts a lot if it falls off a roller.
The only problem with an engine hoist is that sometimes it's footprint won't quite hug a machine, but there are ways of getting around that. That little #25 shouldn't be too hard at around 1000 lbs, that's about like my metal lathe and I can just about walk that thing around the neighborhood for exercise on an engine hoist...
Forklifts and tractors are of course very nice to use if you can wangle one from someone.
Also, watch some machinery moving videos on Youtube for ideas. Plenty of guys using rollers and tilt trailers there.