Good afternoon!
may seem a simple question Yes but they always bring confusing answers! Above all from me!

I think like Oiler!
The way I do:
I want to lubricate my engine, but I do not want oil sucked back in my boiler => so my 1/4 turn valve is coming before the oiler & then the engine.
I need to lubricate my 1/4 turn valve also (stiff, old, leaking,....) I add a valve on top of my boiler.
Concerning the condensate, I do not worry; I built up my pressure to 3 bars. I open toward the engine and blow the sh.. out of it until no water spits out , I partially close the valve to keep heat & oil streaming inside the engine.
When I am over, I isolate/close the boiler's top valve. I open the oiler and I suck the oil out while it is hot.I leave the oiler opened to atmospher.
When I get home. I blow compressed air inside the oiler to run the engine dry.
When no water coming out , I can open my boiler and hear : pssssssssssssss! But no oil sucked in it!
Note: oil inside the boiler does not hurt. It is even good I would say, as it will make a "blanket" inside, between steam & H2O and will avoid to suck wet steam when opening toward the engine. (pressure decrease)
The only problem is that you need to clean the water gauge sometime.
Remember the Greeks having a pack of rope soaked with oil, they put in front of the boat to avoid sea water spraying around. Same as inside your boiler.

Somebody would be able to explain this better than me!

Do you to see inside a boiler????
http://www.youtube.com/watch?v=tI3tWuSsX7c&feature=player_embeddedRegards!