Questions posted to this Forum are by definition not stupid. And we're all rookies in some way.
Poster mentions making a 400-mile trip 3 or 4 times a summer. Not something I'd want to do but to each their own.
For a trip like that trailering a tractor there is a way to be certain your chain binders are holding.
Step 1 is to make absolutely certain you have an air compressor at both ends of the trip.
Load the machine for transport and get all chains hooked loosely. Then let half the air out of all tires. Bind the unit down just as tight as you can. If using flip-over or eccentric load binders tie the handles with wire. Refill tires to rated pressure after machine is fully tied down.
At the other end of the trip, release tire pressure, release chains, refill tires, go to work.
During the trip, the chains will have been pulled so tight by the tire pressure you won't need to worry about things coming loose. By the same token, you won't get those chains loose without letting some air out.
Please post back your continuing experiences so we may all learn.