The lightest option not always being the best theory is simple, not every scenario makes weight the critical factor. For racing, more often than not aero is faster, for more utilitarian type riding, you really are not pushing the bike hard enough to feel a weight difference so if you can have a more foolproof/durable set of wheels you will likely be much happier in the end.

I would not call the A23 worse than the Dyad, just different. I am actually a huge A23 fan but the A23 is fairly light more performance oriented rim. While it is quite durable, the Dyad is still built to be tougher so it could handle incidentals that always come up in commuting better. Things like repeated pothole abuse, having a bike get knocked around in a rack, etc all are things the Dyad could take more of before giving than the A23.