I have worn out only one of these bearings, on a Poulan WT. I'm pretty sure now it was because I used to run the chain SUPER tight. I didn't know any better at the time.
I only really learned about the bearings when one failed. Saw (MS 250) wasn't running right, little 'fingers' of the plastic bearing cage were sticking out near the washer. Figured something was wrong. Fortunately, it did not cause other damage.
Later, I learned at a training seminar how to service them proactively - pretty simple thing to dab it with grease when cleaning behind the drum (STIHL) or to shoot a little grease through the crankshaft hole (Husqvarna).
It easily passes between the crank/sprocket drum/bearing/clip and washer or whatever setup there might be with small openings. the oil is flung all over the place. It gets in there, believe me.
I get it with the bar sprocket nose, because the chain passes over the sprocket and the oil can drizzle in along the sides to the bearings. I might accept that it also works with the clutch bearing if the inside of the clutch drum, the clutch, etc, were covered with an oil film when I took them apart.
I'm going to stick with the dab of grease.
Philbert