Avoid truck freight at all costs. 0.10/lb is the standard insurance. Imagine getting a settlement for $300 your wrecked 10ee....
What I would attempt to do is find somewhere that you could temporarily store things (moving + storage "pro-movers") comes to mind and load them all into a semi truck with a rented or hired forklift in 1 single event (tarped LTL load which would probably be around 1/3 to 1/2 of a semi truck's flatbed). I would crate anything you cared about, you can reuse the osb later for something or other, thru-bolt (note not lag bolt) to 4x6 timbers for the anti-tip-over and also so you can either use a pallet jack or forklift to move them around. Also have to carefully consider tie-downs in your crate building, for example the 10ee should probably have a padded strap go over the bed, so save old pairs of jeans and cardboard, cut slots or windows in the crates where needed. I also bought cans of LPS3 and sprayed down all of the bare metal surfaces because humidity can do strange things when you aren't looking.
I have sold machines before to move and always wished I didn't. Seems like they sold for 0.5x of what I thought I had and cost 2x to replace, or the replacements were equivalent cost but despicable condition. I'm not the worlds best salesman so that may have something to do with it. I don't know CO specifically but it seems like manufacturing is not "all around".
Also I built several crates on top of regular pallets, which were framed inside with 2x4s and had independently supported shelving for stacking up heavy stuff, iow your arbor press could go in there, chucks, steady/follow rests, steel stock, corded power tools, you name it. The independent shelves were for making it so the bottom items weren't bearing all of the weight of everything above. Center post on each shelf. Cut one "wall" of the crate in half so you can load from that side. I used a roll of brown kraft paper for packing material. Also made notes in a notebook of where every item was and in which crate in case I had a situation where I had to have tools *right now* and didn't have the luxury to unpack it all searching for something specific. I put all of the corded power tools on the top layers accordingly.
I would consider crating the roller box, in that condition it looks like a plywood crate and not a bling-y thing that all kinds of sticky fingers are going to want to have in their shop...
When you get where you are going, you'll need to rent a forklift and have it coordinated and waiting for the driver (get truck driver's cell and stay in reasonable contact with him) so you can take it all off the truck and he can go search for his next gig. Also may be able to use the services of a pro "moving + storage" and have them intake it all at once, then you just extract one piece at a time until its finished.
I moved the total of around 2-1/2 semi trucks of equipment this way, although some was with my own truck and gooseneck trailer. Some was dealing with monkeys from uShip, I seemed to find the worst of those. I've found the semi drivers to be so much more professional than those idiots who got a dually + gooseneck from their Dad so they'd get off the couch.
One thing that's helpful is to create a spreadsheet or list of everything you own and then attach a weight to it, even if its a SWAG or a google-lookup. Then when you start contacting LTL companies you can have an idea of the weight involved. It plus the square footage are the key components to setting up the deal. The nice thing about LTL is once the driver leaves with your stuff, its never going to be touched until it arrives again at your location. They might haul something else that's going the same direction. But not like truck freight where it could be loaded and offloaded, several times, by people driving forklifts at full throttle in both directions and doing 50% of the work like a bulldozer. Every time I go to a truck freight terminal I fear for my life....
Best of luck to you, its work for sure but its very nice when your shop is setup in your new space.
Some thought starters...just before the tarps went on. Transporting the forklift is another issue that I didn't specifically address....but I have ideas for that as well.
