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Doesn't really matter, its the same way that houses are moved, just a scale issue, prinicple is still the same. just size winch, trailer, logs to the shed size.
BTW a 40x40 isn't really a shed, its a barn or pole building which still can be done,, just a lot more work.
I have a shed that is 30X40, the barn is 30X60.
Yes! It does make a difference. Small aluminum prefab shed 4X8 or so, you get a couple guys and a pick/up tilt it over into the truck, strap it down and head for the house. A larger stick built shed well that's when you get into winches, jacks and specialized equipment.
Besides the OP in a response has stated she doesn't have the "shed" yet, and has no idea what it will weigh, how it's constructed. Once again, until it's definite, it's hard to say. A prefab 8X8 aluminum shed from Sears and Roebuck won't weigh 500#. But you take an 8X8 stick built with asphalt shingles that's a whole nuther set a tools.
As described the one she is presently looking at is 8X12, built on a floating wood foundation. Care to guess how much more that weighs than a prefab aluminum of the same size.
My advice 8X12 stick built on a floating/skid foundation. Look in the yellow pages, call a sales place that sells the prebuilt wooden sheds. They usually have a contractor that handles deliveries and moving. I have two portable sheds built much like the OP describes. One 12X18, the second 12X20, wired, finshed with sheet rock, A/C. had them both moved 20+ miles, for about $300 & $350 respectively. No way would I attempt to move these things myself. I have a large trailer that would have handled the weight, but those guys went picked up the buildings brought them to my property, unloaded them, set them level, all before noon (one building a day, not both on same day). It would have taken me atleast a very long, dangerous day to get one jacked up and winched into my trailer. Not to mention I don't pocess a over sized load permit.
The cost of both buildings plus delivery was under $3k. 12X20 cost $1500 + $300 delivery (insulated, wired, finished sheet rock, lighting, tile floor, work bench, A/C) 12X18 cost $700 plus $350 delivery (insulated, wired, plywood interior walls, lighting, work bench, A/C and heat). No way could I have built comparable buildings for any where near the same cost.
So yes! I do know just a little bit about the subject.