Thank you for your answers! Very helpful.
May I ask why rough out? So pure cement/glue construction is best for keeping the water out? A lot of the rugged boots involve some type of stitched construction with plenty of cement, as far as I can tell. One example would be a boot with a leather midsole and a Vibram Christy sole cemented/glued to the bottom of that...
I simply asked for them to be "resoled," and assumed that would mean a full, new sole. Perhaps that was a bad assumption on my part.
I am assuming you literally will wear them outdoors for outdoor activities, instead of being an urban woodsman.
Rough out just so that leather scratches can be fixed/concealed easily. Leather choice is important too, your typical dress shoes leather is no good.
Good water proof shoes are usually turned-out, stitched down. Or at very least storm welt with rubber sole. GYW or HW will get you wet feet 100%.