This is a very broad question. Really it depends on the quality of your bearings, and which ones are exposed. Also if you have any amount of grease in them. And the quality of your oil.
If you have flushed stainless steel bearings I'd say every 3-4 trips, one drop each. If they have grease, then probably more.
Now ceramic hybrids are pretty forgiving, but you don't want to just forget about em. They will rust and get rough. I've seen some with the outter races pretty bad, and that makes them rough under a load. But they seem to always clean up enough to cast. The ceramic balls never corrode, so they will almost always spin.
I use ceramic hybrids and I usually know when to re-oil by the sounds of my casts. When they start to "hiss" real loud then I know they are dry...Just a TINY drop of VERY low viscosity oil in each.
Ok thats enough...I'm goin overboard now.
Everyone has their own opinion, this is just what has always worked for me.