Hmmm. Sounds complicated. Might be easier to just sell the IJ to me
Seriously though, I have shipped machines before and had them shipped to me, never done it both ways. I don't think there is any real trick to it though. At the end of the day a freight company is a freight company with all the same risks. The most important thing (imo) is to make sure both machines are packed really well. Shrink wrapped, blanket wrapped, corner boarded, shrink wrapped again and strapped on a decent pallet. I have a couple of Stern boxes that I keep around in case I need to ship a machine, and in that case I just shrink wrap and pack in the original Stern stuff, strap it to a pallet and am ready to go. Wouldn't work for WMS games of course.
I've had experience using NAVL/STI when shipping a machine up from the States, but not within Canada. Still, it might still be worth calling Michelle Bianchi who is always referenced on Pinside as the go to person for shipping pinballs, she might have some suggestions/options for white gloving it where someone comes in and packs it up, but my guess is those guys can be hit or miss as well.