On the receiving end - from on top of the truck, looking down into the basement
One chain is anchored to the tie-down hooks on the truck. The device in the middle is a 3/4 ton shop hoist
The drill press is strapped to a tree cart (a kind of hand-truck specifically for moving balled & burlaped trees); a second chain is anchored to the handles of the cart, and is hooked to the hoist. One set of planks leads up to the lip of the hatchway; a second set is laid on the stairs going down to the basement
Set up and in position. Courtesy of the wheel, the lever, the ratchet, and the inclined plane!
At the originating end -- the house at my parents' nursery -- I used the front bucket of their John Deere loader as the anchor point. Being able to have the hoist elevated and thus able to pull the cart straight up the planks was a huge plus.
This was my grandfather's drill press -- a Craftsman 150 from the 1960s. In his semi-retirement he had assembled quite a woodworking shop in his basement (table saw, scroll saw, radial-arm saw, band saw, planer, and drill press). We have several of the pieces of furniture he made, including the table we eat at every day. Getting that drill press muscled into place and turning it on for the first time was surprisingly emotional for me. I was feeling so very connected to "Pop", yet also feeling very strongly the irrevocable finality of his passing.
He would be happy to see it being used. Happier still to know that his grandson was using it to make toys for his great grandson.
Rule one: don't die