Nothing quite worked today. I think I’m slightly worse off today than I was yesterday.
I got 60 feet of 3/32″ steel wire, a couple of pulleys, miscellaneous wire-related hardware, and a 4-wheel heavy-duty cart and headed to my land. I tried to build the cart, but quickly realized I didn’t have the necessary tools. So I headed to my trailer, with cables, pulleys and all.
I turned my trailer around so that it pointed up the dirt road, but when I did that, it started rolling back downhill, and across the dirt road. Instead of being in a nice clearing off the road, my trailer was blocking the road, and a few feet farther from where I wanted it than when I started.
No matter, I’ll just pull back up, with the pulley. I wired everything up. One end of the cable was secured to a tree, one pulley attached to the trailer hitch, the second pulley attached to the tree again, and the end of the cable tied to a 2×4 for extra leverage. It didn’t take long to find a number of critical flaws with my plan. First of all, the front post of the trailer (which prevents the hitch from hitting the ground) dug into the ground and acted as an anchor. Secondly, the two pulleys didn’t reduce the required force enough to really move the trailer much. 
Lastly, and most fatally, even when I did manage to move the trailer a few inches, I had no way to secure the gains I’d made. As soon as I released tension on the cable, the trailer would simply roll back to where it was before.
So, at the end of the day, I’d only managed to get my trailer to an even less convenient location. But no matter. Lesson learned. Tomorrow, I’m going back with a winch-type contraption that’s supposed to be able to pull a ton. The cable on this contraption is only 12ft long, so it’ll take a while, but that’s ok. I’ll get there; 12ft at a time.
Laptop and a Rifle 
I suggest breaking down and getting and getting an old, cheap 4×4 pickup and a chainsaw.
this is why i prefer rope to steel cable. with rope, you could tie knots to secure your gains, and also you can grab the rope with less fear of slicing off your hand. i would put a stake in the ground, pull on the rope and then tie it around the stake (by which i mean just wrap it around the stake a few times), then go block off the wheels before re-tying.
are you using the most efficient pulley setup? with two pulleys, you should be able to reduce the force to 1/3 the rolling resistance of the trailer using this setup:
be wary of only reducing your force by half by using this less efficient setup:
which looks like what you might be doing since you’re pulling in the opposite direction from where you want the trailer to go.
Ah, you’re right, I was using the less efficient set up. I think I was only getting 1/2 reduction. I don’t think even 1/3 would’ve been enough though. I thought about using a stake of some sort, but it’d have to be a big fucking stake driven pretty far down. Then I’d have to pull it out again. Yeah…
I went and got a winch type thing, which worked great. I’ll be doing a post about that soon.