If the PO towed and launched with the outboard down, like your picture shows, maybe he did pull the boat ahead on the trailer just to keep the outboard skeg from scraping on the ramp.
Personally, I think it is a bad idea to tow a sailboat with the outboard attached and even worse to launch it with the motor down. I know there are plenty of people who do it, but that kind of weight on a trailer with almost no suspension, will eventually crack the transom's fiberglass. Powerboats have reinforced transoms but sailboats don't.
- Will (Dragonfly)