I would say that cost would be a factor.
You could stock up on some go-to or everyday smokes without spending a lot of cash or even when all the sales were going on.
For me it depends on the smoke. I have some certain cigars that I will buy no matter what if I find them. I don't ever plan on selling them but just trying to keep a good stock of them for the long haul.
Not sure what I would call a lot? Maybe Eleventy Billion.