I Lay a cigar out on the counter overnight.  Improves every aspect of the smoking experience.  
Naturally, I do not make allowances for the preferences of others, this is how I DO IT.  But I 
had my first bad draw in maybe 50-75 smokes the other day.  Sale stick, du Dauphin, so like 
Bobarino, I call that a manufacturer's defect.  
In answer to your specific Q's, a week might be too long, a month probably ruins the cigar, 
but never say never.  PLANNING for smoking is more of a harvest of ready to smoke sticks.
I would go through all my stock, pull out a flaked wrapper here, a hideous wrapper there,
a particularly oily cigar in another box, then I put them all in a desktop.  When I want to smoke
a couple of cigars over a weekend, I might pull out two or three for that and lay em out overnight.
If they don't get smoked, I just toss em back in the desktop.  For those who posted and stated that
they do not want to be restricted or over-planned, I think that the desktop in the middle of deep
storage and "a night on the counter" is a good happy medium.  And I'd be lying if I said that
I ALWAYS DRYBOX. 
