Which sailing rig . . .

I've got a feeling sailing boats with more than one mast always look better if the shorter mast is nearer to the observer.

A ketch sailing away, looks terrific. So does an approaching schooner. Neither vessel has quite as agreeable an appearance when the sails on nearest mast obscure the further mast's canvas.
 
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Having bits sticking out either end can be a problem. I saw a photo of a boat with a generously sized bowsprit poked through the window of a dockside restaurant once. A gust of wind at just the wrong time, IIRC.
I think it was Adlard Coles or maybe Ransome who with an unusable rubbish auxiliary skilfully tacked the Racondra into harbour and then swept the bowsprit through the dockside railings and demolished them. If it could happen to those crew.....
 
I think you're right. Such a pity wonderful looks don't accompany ease of ownership...

...the more bother the rig is to work, the more pleasing it must be to see go by.

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That just doesn't do it for me, but couldn't say why. If I were ever to be rich enough that running costs would be pocket change, I think a gaff schooner might tempt. Or maybe something from Spirit

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But I expect I'll be sticking to my little Snapdragon. Ah, well...
 
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