Hi Orgnoi1,
Sorry, I can't see your pictures (work firewal thing), but I trailer my 440B all of the time. I use the factory tie down points on the rear (the slots in the rear axle frame gussets), and a single chain to the bucket / attachment on the front of the machine (bucket lowered flat to the floor of the trailer, of course). I tighten up the chain to the front of the machine first (by backing up the machine), then load binder the rear chains. My chains are all 3/8“ grade 70, which are likely over kill for a 2500 lb machine.
This seems to be quite legal for Ontario, where I have been moving around farm equipment and heavy equipment for 20+ years.
If I was required to chain down all four corners, there are slots in the front axle frame gussets that I would use, same as the rear.
My $0.02,
SR