ian. If you were to incline the boat whilst oiling the shafts then i would fully expect the top of the shaft to recieve lubrication when filling up !
Moreover, if the tube extension were to stay above the top of the shaft (when the boat is horizontal) and oil were to remain in this tube at a level of the top of the shaft then this would also guarantee lube staying at the top.
Dont bother with oil myself, just a few drips either end before sailing. I prefer nylon bearings as they are self-lubricated by the water gushing through..
Ashley