My 2 Cents.
Oil will penetrate into the surfaces of the sleeve and prevent the rust. Freshly bored cylinders however are 'virgin' and will rust right quick, especially after washing with soapy water. Also they are open to the atmosphere.
Now an assembled engine is oily, carbony and reasonably well sealed. Rust doesn't occur on the cylinder walls for a long long time in this condition assuming they are stored indoors in a fairly stable environment.
However, if you start the engine up and don't warm it up fully (aka, don't drive it more than 30min), you're actually introducing moisture INTO the engine that then can't escape.
It's better to just let it sit realistically speaking. If you are especially paranoid, use a engine fogging solution when you winterize it. I think I use Stabil brand fogging oil, no problems yet. But then again, I have one engine that literally sits outside in a snowbank all winter long every year and hasn't seized yet - fogged or not. (A free lawn mower that I hate and have been trying to kill for years...
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