Or get it on it's side and just winch it on a scissorneck? No cranes, hoes, or anything else needed that way and it would be a lot cheaper then $3k if it's a short move.
You have no idea what you are talking about.
He's supposed to somehow get 30,000lbs from upright to on its side, and drug on a trailer, with no crane or hoes or anything? Is it just going to fall over? Have you ever tried to drag 30,000 of dead steel box onto a trailer? How is he supposed to get it back off? Hook a chain to a tree and drive away? If he's going to end up destroying it, he just as well scrap it where it sits, because there won't be anything left of the caboose when he's done. And will have ruined a trailer deck in the process. And I don't think the idea here is to destroy/ scrap the caboose.
You can get them on their side on a trailer, but you put the trailer beside the caboose and tip and let it down onto it. And then winch it back off the trailer to upright. With multiple crane/ hoe/ wrecker/ forklift. Which is probably how they got it there in the first place.
Is it on a section of rail where it sits Doug? Or just on the dirt? I like you're idea of jacking it up and getting a semi trailer axle under it. I think if you put the axle where the trucks are, you may be able to have a big wrecker with a wheel lift get under the front and pick it up and drive. How short could you get it if you extended the axle and got the wheels/tires outside of the caboose? Fab up a extended axle out of heavy square tubing? You might be able to weld up something onto the coupler and put the axle back there, but its going to make it tough if you have any tight corners.
Steps aren't bad to get off. I've also seen the top observation deck removed (cut off) for long hauls and then re installed (welded back on) once moved. But you would need a crane for that. But not near as big of a crane as if you want to load it.
I somewhere have a number for a guy that was buying and selling rail cars Doug. I also know where they are moving some static cars to, and making a rail display, and I can see if they are looking for a caboose- if you want to sell it, and then it can be their problem to move it.