Hi Marty,
The greatest satisfaction I have had from ShipSim is docking the Vermaas in Marseille and Hamburg without a tug and snug alongside, there is no way I could get a fast time doing those missions. If you are after a fast time then you play the game differently. Going outside marked channels and so on is something that everyone can do, so I wouldn't consider that a cheat, (it isn't in the spirit of ShipSim but then some of our community have never had anything to do with the sea until now and so wouldn't know any better, I am a bit ignorant of the finer points of guideing a ship on the approaches to a harbour myself), it takes all kinds to make a world. This could be addressed by mission creators by placing waypoints strategically and like TerryRussell only allowing control of different vessels when he wants you to have control of them. I think you may be wrong about there being no penalties for slight damage. When I was trying to get the best time in 'New fast ferry service', if I hit the dock with the stern of the Red Funnel Cat, (above the water line), it caused 1% damage and that was enough to slow the Cat down by 1 or 2 Knots and on the longer missions that is enough to abandon the attempt.
Regards, Dave