It is pretty comfortable. My only issue with it is that Velcro + wool (long sleeved) = fraying cuffs. Had that issue with a watch strap until I could find one that wasn't velcro. So, I ended up with the dog tag one as well, to avoid that problem in cool weather.
Yeah, that's one of my problems. My watch strap kills the left cuff of any long-sleeve shirts I own. I just don't like regular watch straps.