If the seal was toward the case and the open side toward the drivers, then no oil would get onto the bearing until the seal was worn; then oil would leka out of the chaincase. Also, with the open side toward the drivers, dirt would get into the bearing. I wish I remembered my replacement bearings...I think I had double sealed bearings, but if I don't, then I would have installed the open side toward the chaincase for lubrication. Any particles in the chaincase oil would be minor compared to the outside dirt always getting into the bearing. Also, since there is no actual pump in the chaincase, most shavings would stay in the bottom of the case unless there were enough to get up to the level of the bottom of the chain...in which case, you have more to worry about than the bearings. As was already compared, its no different than the bearings in a manual transmission, which are open, and those don't have problems from metal shavings.
I actually think I would stick with one seal and put the open side toward the case. That will allow better lubrication than the double sealed bearings, which tend to go dry fairly quickly (a year or so) in an application where they see high speeds for long periods of time.
Jim