My Dad's old boat was bought by a guy that had little (or no) sailing experience but big dreams of sailing off into the sunset. He bought the boat in Ottawa, put it on a flat bed and trucked it down to Miami. He loaded it up and set out for the Bahamas. I don't know if he checked the weather or how rough it really was but the story goes that he got out a few miles and scared the crap out of himself, turned around, crashed into the dock and never went out again. For some reason he decided to truck the boat (a Viking 33) back to Ottawa to sell it. The holding tank was full when it went on the truck but only half full by the time it reached Ottawa - the rest was in the bilge. The guy that cleaned it out told me a hose came off the holding tank.
I don't know if trucking has harsher motion than being in the water but in this case trucking with a full tank made a big mess. The guy that owned the boat at the time obviously had no idea how to maintain a boat and probably never pumped the tank.
The boat ended up being bought by a guy that sailed it locally and maintained it beautifully which was a big relief to my family. It was sad to see the shape it was in when it came back into town.