I have never shipped a motor to someone else, but I have bought many motors and had them shipped to me.
Its all about the guy selling the motor. If he values his customer he will go to lengths to secure it. If not, you're at his mercy. I have had some come packed in a crate and arrived perfect, and others were shrink wrapped (you must be kidding) and it arrived in pieces. However, in that case I complained so loud that he gave me a refund, so in effect it was a free motor.
Small outboards.com probably would be of no value. They sell new motors in factory packaging and they ship FEDEX.
The choice of shipper is up to the seller, not the buyer.