I had to learn the hard way. I've bent kickstands because of improper trailering. I've had a bike fall over and dent the gas tank because it was improperly strapped in. I have friends who have blown their front fork seals from over tightening the straps.
The seller might have thought I was overly cautious in my trailering techniques. He was kind enough to help me load the bike and strap it in.
Ultimately I let him go while I continued to fiddle with the straps and ratchets. He had trailered bikes for short distances, I don't think he's trailered them for four hundred miles.
Getting the bike into the trailer took just a few minutes. Getting it secured may have taken another full hour.
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