Having worked for a few years in an electric motor rewinding shop I will add a few things.
Not many bearings are made to be oiled nowdays. That doesn't mean oil won't help them. However, oil helping them and being designed for oiling are two different things. Often, adding oil to a sleeve bearing (typical fan bearing) will help, but it will also attract and hold dirt. Ideally you want to disassemble the fan so you can remove the clean the shaft where it rides on the bearing. If you're REALLY motivated you can swap the bearing from end to end. One end usually wears faster and this will distribute the wear.
I'll never forget this one fan. It was for a grain silo. It ran on 480v 3 phase power. I sat on it when we fired it up. It started skidding across a ROUGH concrete floor. The weeds/trees across the parking lot, across the road, and in the ditch (probably 100' away) started whipping around as if blown by tornado-force winds.
When you oil these things, you don't want oil running out. That's just asking for dust problems. Just add enough where it is still being pulled into the bearing area, and stop before it fills up. Allow it to soak/wick into the bearing before running the motor.