Generally, every cigar *should* benefit from dry boxing. CCs tend to smoke best in a state of current lower relative humidity percentage (60%'ish), though definitely store them in your humidor around 65%-70%. Personally (and this is just me; others can chime in with their own experience), I've found that everything from Archetype gets much better after time in The Box. I enjoy the Drew Estate Undercrown Sungrown quite a bit. However, since I moved over here they just haven't been the same. Can't tell you why. I decided to dry box one for a little over a week, and it came to life just like I remember them being. So, I box every one of those I smoke, now. There's a thread on dry boxing around here somewhere (search it out) with a lot of good information. I personally haven't found a cigar where I said, "Man, I wish I wouldn't have dry boxed this", once I was done smoking it. I've had quite a few where I wish I DID box it, though...
*EDIT* As for how I choose what goes in the dry box, since it obviously takes some of the spontaneity out of it -- I have an old humidor with space for about 40 cigars in it. I usually keep it stocked with a little of everything, and throw ones in there that I know I want to smoke soon. Normally, when I take one out, I replace it with something else. I also have a small tube of 60% beads in there, as well.