Quote:
Originally Posted by BamaSpek
I have a 8x16 and an 8x10 wood shed that I need to move. The small one has secure skids the other one has one skid and another Kinda on there.
The both have bolted down wood shelving inside that im sure adds a bit of weight. Shingled roof.
I need to move them about 300 feet across fairly level dirt/cleared land.
Ive considered three ways:
1. Drill a hole through the skids and adding rebar or something to tie a chain to and dragging them.....but not sure my tractor has the arse for it. Its an 8n....I'm afraid if I pulled it tied to the rear of the tractor the front would raise....and reverse on this thing is somewhere near mach 3.
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Am I over complicating this.... 
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Yes, you are overcomplicating it.
Option 1 is the only easy, simple one. You have the tools to do it.
Go slow, plan, think before you act. That keeps you safe.
Take the small one first, smaller & has good skids. It came with skids so - it can be moved.
I'd put a chain on one side of a skid (anyone with a tractor has a 14-20 foot chain laying around, right???) to the hitch of the tractor and back to the other skid.
I'd nail a 4x4 or couple of 2x4s between the skids so they don't pull together. Bracing. Perhaps your shed has that already, but doesn't hurt to do it more.

Don't pull from the middle of this bracing - you need the chain (cable, strong towrope, etc) anchored to each skid. Does not work to tie to the bracing in the middle, just pulls it apart...
The N series tractors were a little tippy. They had a bad design on the hitch setup, allowing a person to pull from higher up.
To keep it safe, attach the chain low on the tractor. You want to be pulling from well below the rear axle. I don't know if you have a fixed drawbar or a bar on the 3pt, but keep those things in the _low_ position and then the tractor will spin it's wheels if it can't tow it. If you pull from high up, the tractor could flip over backwards instead. It is basic geometry, but just keep the pull-point low and all will be well.
The 2nd shed likely will need a couple 2x4s or 2x6s added to the bad skid to beef things up, whatever scrap wood you have around (homesteaders always have a few sticks of scrap wood around right?).
Should work the same way. That's a real short distance, no need to involve lifting these with a trailer or truck.
Takes longer to read this message than to actually do one.
--->Paul