Wasn't your last boat an I/O? You didn't winterize it every year?
No, OIL doesn't freeze............. I doubt it has a closed loop system, if so it'd be running anti-freeze (like a car) and wouldn't HAVE to be drained every winter.
Nobody, including you apparently, know what motor is IN YOUR boat, so Bondo was being general:
Drain all the water (there are many places/locations to drain depending on what motor YOUR boat has) and leave the plugs OUT of where ever you've drained water. They're called drain plugs because you occasionally drain water out of them.
Your motor & exhaust manifolds both probably use lake water for cooling, so you've got to get the water out of it all. Compressed air can also be used to blow out passages & make sure there isn't any water left behind.
W/out water, the passages in your block are filled w/ AIR & as Bondo mentions, air doesn't freeze, so there is nothing left to harm your motor..........
BTW: Lots of good info in here, look around, you might find the answers before someone has a chance to answer them for you.
Here's a thread about winterization, w/ a link to another thread about winterization. Bondo posted the same info in those that he has here in your thread...
winterization with compressed air