Well for the boat shoe i will definately go for the boat sole, i have owned many boat shoes in the past and i really like the style and comfort.
But i am also planning on buying a pair of 4 eye camp moc. These shoes will be shoes that should be comfortable to walk in for several hours in urban areas and i dont really know the difference between realtex lactae hevea, plantation crepe wedge, mini lug, tempest, or cristy. Will the sole affect the stiffness of the shoe?
Note that i also live in Norway, and that i tend to wear the same shoes whether its winter and - 10 celcius or summer and 20+. In the winter it gets snowy and it gets a bit slippery outside, so wont buy leather soles for example. It would be nice to have a sole that can handle wet and slippery weather, but at the same time does not looks like you're going hiking and can look good in a smart casual business enviroment (shirt and chinos for example).
next fall i will probably buy a blake chukka or a 5 eye winter suade boot that i can use when the weather gets a bit nasty aswell, and it would be good to know what sole i should have on those too :)