Nice post by Mark the OP.
Hobbies are supposed to enhance our lives with fun and inveraction. Most aspects of ours does. The downside of the "slide" is that it can addict those so inclined to an ever increasing load of purchases. Good news is that you can always resell them without significant material loss if you buy right.
One contrarian point that has only to do with timing. If as part of "your plan" regarding prudent cigar purchasing you anticipate and budget a larger than normal portion of your budget in the "now to christmas" period, much $$ can be saved by significant sales.
Or you could be homeless my January.