"Tom, 4 stroke motors are stil
"Tom, 4 stroke motors are still pretty much a "new invention" to most of us on here - so your questions may tend to go unanswered.
I do have service manuals for 4 strokes and did have a read through the one pertaining to your motor.
It appears to have a system much the same as a car - oil sump/pump which pumps the oil at about 27 psi up through the filter, into the journals and ultimately to the cylinders.
Since the sump is below the powerhead, and fed to the pump via a pick-up it would lead me to question why oil would be in the the cylinders (and leak past the rings) when the motor isn't running, unless the motor was pretty close to being upside down (???)
All I can compare your situation to is a normal vehicle - if it smokes when you start your car, that's usually the first sign of the rings starting to go.
Perhaps though there is someone here who has experience with 4 stroke outboards and can add their opinion.
The only other point I can pass along from the service manual is - if you are operating the motor in an area where the temperature is consistently above 40 degrees (F), then you should use 25W40 oil as opposed to 10W30."
A "professional" is someone who gets paid for their work - it doesn't necessarily mean they are good at it :)