Bigger is better. Get the biggest winch you can afford. You can load light stuff with a heavy winch, but you can't load heavy stuff with a light winch. Also, as someone else noted, power out is a very useful feature for unloading. A decent winch will also have a clutch to release the drum when you want to pull the cable out quickly.
As Old points out, cheaper winches tend to be advertised based on how much rolling load they can move, not on the actual line pull. Also, keep in mind that the rated capacity of an electric winch is based on the first layer of cable wound on the drum - as the drum fills with cable, the diameter increases and line pull decreases accordingly.
As far as an on-board battery, any trailer big enough to need a winch to load will also need electric brakes, and the winch battery can be used to supply the backup power to the electric brakes. Mine is wired to charge from the tow vehicle, just like the battery in a travel trailer. I prefer to have a separate battery just to ensure that I never inadvertently run down the tow vehicle battery.
I have a deep cycle battery on the trailer, and have never run it down loading something, even when we had to use the winch to move the load around before pulling it up onto the trailer. I also almost always use a snatch block with anything heavy just to slow down the speed, plus it also cuts the load on the winch in half.
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Today's Featured Article - Old Time Threshing - by Anthony West. A lovely harvest evening late September 1947, I was a school boy, like all school boys I loved harvest time. The golden corn ripens well and early, the stoking, stacking,.... the drawing in with the tractors and trailers and a few buck rakes thrown in, and possibly a heavy horse. It would be a great day for the collies and the terrier dogs, rats and mice would be at the bottom of the stacks so the dogs, would have a busy time hunting and killing, all the corn was gathered and ricked in what we c
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