A friend of mine transports his 2 stroke jet on its side (carbs up) with oil remaining in the motor. Hasn't ever had a problem.
I used a my new 4 stroke jet last year and did the same transport. I was reading my owners manual and it said to drain oil first before a transport as it could enter the cylinders.
So, how bad have I screwed things up. 1 move with oil. How can I tell when we have no ice?