I know you are just talking about taking the sharp edge off a piece of decking. But I'm intrigued by that step - breaking or easing the edge - taking a block plane or piece of sand paper, and putting a final edge on a finish piece. I think it's like a finger print that a craftsman leaves. It sounds simple, and it can be. But often it's a personal step that a furniture builder, cabinet maker, finish carpenter or boat builder say, has refined. I look for that finger print on work.
It's easy to over do it. For instance many people new to wood reach for a router and overdo it. It all depends on what they're doing but many nice pieces I see have been touched by a sharp plane. And the experienced user gets a consistent, tiny chamfer. Or some will put their own shape, unlike a round over bit, their shape will be custom, tiny, understated. It's always a very small detail in comparison to a machined edge.
I'm thinking with the decking to not ease the edge where the pieces will be caulked, for the sharpest caulking lines. The caulk will contain the sharp edge and the caulk stands a little proud of the wood as well, protecting the edge. What do you think?