this has been my philosophy for quite some time now, as well. while a few years ago i arrived at the point where i decided to not 'settle' for everyday cigars that are mediocre and upped the ante to smoke only good ones (at least by my estimation) i reserve friday nights for special cigars. last night was a CC punch churchill, ABR 04, which btw i'm still waiting to open up. unfortunately remains an uneventful smoke...
Again. I wasn't really saying only smoke premium cigars. I see nothing wrong with smoking a Sancho Panza or a 5 Vegas when cleaning out the garage or playing poker with the guys. In any situation where I will not be concentrating on enjoying the cigar but would like to have one anyway the everyday smokes are just fine.
My point is if you can afford it don't just buy a 5 pack and have 1 each for Thanksgiving, Christmas, Superbowl, Birthday, and the last on vacation. Have enough to melt away a bad day or week too. Get a cigar out that will completely distract you for an hour or more. In my opinion, there is no reason to be in this hobby if you can't use it when you need it most.