I would estimate my current stock at around $X,XXX - $X,XXX. Obviously you can still tell I'm in the <50 box category, but dollar amounts are just numbers, and it comes down to what each of us are personally comfortable with.
This is how I look at it, would I rather have X amount just laying around extra in my bank account doing nothing or would I rather have that in cigars to enjoy? At my current amount, I would rather have the cigars to enjoy. When X amount becomes large enough, where for my personal situation, I say "Oh ****, that's a lot of money!", then I should back off.
As far as my wife is concerned, it's D.A.D.T.