Curious. In 1939, I would always take the Channel passage. I've always been able to get through the channel in '39, and there's almost always several lone merchants to pick off along the way (just avoid undo commotion while actually passing through the Calais gap - I slip through there submerged at night, and quietly).
If taking your route, I'd take a bit of a side trip down towards Isle of Skye - always some lone merchants in The Minch or moving through The Little Minch.
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