The seals are put in to keep the water out, but not to keep the oil in. That's why you have to top the bowl off all the time. If the shaft was worn where the seal rides, it would leak all the time (even when it's just sitting), and not just when you run it on the trailer. The oil probably just got a little warm in the bowl and expanded, creating a little pressure that forced some of the oil through the seal. I wouldn't worry about it too much, unless it continues to do it, even when you're not running the boat. And next time, so you don't have any pump issues, you should disconnect the drive line when you run the boat on the trailer, it can also screw up your wear ring tolerances, if you do it too much.
