Although I've not shipped a outboard, I have shipped other large, 100 lbs+ items which were very fragile via UPS. I packaged it very well, crated and strapped down, and paid for the extra insurance - no issues. They have required a crate for larger items though and you want to be sure you tell them its a gasoline engine which has of course been drained of all fluids. More than likely you'll meet their freight quotes.
I have shipped a Briggs 5 horse via UPS. Went OK. I self packed with no crate. Used a mangled original Briggs box with a bunch of tape. My driver looked at me funny, but he took it. He kinda knows me so that helped.
Gonna move this to non-repair OB. More OB freaks over there . . .
I've shipped thousands. About one out of a hundred suffers some sort of minor damage. However, I only ship new engines that are completely dry of fuel. That's a requirement for the carriers. The gear oil can stay in the engine as that is a sealed system.
I've shipped and received my share as well. UPS sucks big time. Whatever you do, DON'T have them pack it for you. Disaster waiting to happen and they will fight any reimbursement for insurance (my experience).
Go to U-Haul and buy shipping materials. Pack it well - use common sense. Ship via Fedex ground home.
I cut 2 sheets of 3/8" plywood and have it banded with a steel band and some wood cross supports and wrapped it in heavy plastic and tape....... I have shipped both ups and fedex that way.