Yeah well thems the breaks I guess.

Perhaps your method of drifting them on got better with the practice.
Bearings are designed to work using grease unless they are an open cage design specifically meant for that kind of operation. As I said oil will dilute the supplied grease and is not designed for the punishing loads found in the bearing. What are you using? Singer oil? Motor oil? I use the cheap throwout bearing and generally get a number of years out of them without resorting to modifying them. I've had a number of years dealing with bearings in industry was my job.
I've added grease to known culprit sealed bearings before as they are typically pretty cheap with the grease. Adding too much leads to the grease being ruined by the clay separating from the oil, and to little grease leads to overheating and failure. I usually can work out how long the bearing will last on a known piece of equipment by how well I feel that I have installed it. A tap in the wrong place or incorrectly pushed and aligned bearing will easily take 25 percent of it's lifespan, ad that's just a minor fault. If I muff it up completely, I will expect to be back there the next day.