Out of high school I worked for a seed corn research facility. I drove equipment all over. That was with a real tractor and not an over sized lawn mower. I'd take the time and load it up. I drive truck for an imp dealer so I get your point on time of hooking up, and chaining down, but then it's done and safely in your yard not on the side of the road the road trying to winch it on a trailer.
You can be the safest person, take all the safety precations but $h!t can still happen. 2 years ago I was working construction un chaining a skidloader off a trailer on a no name hardly any vehicle street. Harzards on the truck, trailer, cones surrounding the area, men at work sign, vest on and a 16 year old drove through the cones, onto the trailer, came off, ran me over and dragged me. I wasn't even landed from med flight and what was left of my phone I had a voicemail from the parents insurance. Asking if I had a vest on and cones out trying to put the blame on me if I didn't. Luckily I did EVERYTHING correct to cover my backside and my employeer,but I was laid up for 2 years almost lost my hobby farm, drained my savings, and checking accounts, and missed some good times playing with my son. Insurance doesn't make money by paying settlements. Even if someone hit you, you're guilty until proven innocent by Insurance. I look at it as this. If you(anyone) needs to ask if something is a good idea on here it probably isn't...........