...do you think it's even possible for another cigar boom to happen?
The conditions that brought about that particular boom are probably unlikely to reoccur. However the 14 years from 1900-14 must have seemed quite different from the 14 years from 1925-39, but the wars that followed must have seemed remarkably similar to those who suffered in both, at least in terms of loss and hardship.
So, if you will allow me, I will rephrase your question to a more personal level: "Is it possible that there will come a time when I am unable to buy cigars I enjoy at a price I am able, or even prepared, to pay?"
If you live in California, notwithstanding any availability over the Internet or your contacts in the world of organized crime, that possibility came realistically close recently, merely through proposed tax increases. The market is balanced at the moment, and mostly the people who influence the market on either side of the law of supply and demand want to keep it that way.
The 14 years we are now in are characterized by large multinationals whose goals are best served by stable markets. The smaller producers have their risks spread through contract manufacturing for 'brand only' distributors. Some brand owners may encourage their tiny sector of the market to overheat, and every producer wants a very profitable premium brand to sell like hot cakes. Producers and vendors generally want to nudge consumers gently in the direction of higher priced lines with higher revenues and bigger profit margins, but these conditions rarely drive markets into boom conditions. Additionally, provided the market has capacity at lower price points, the consumers can shift their buying patterns accordingly. In an ideal world that tends to make for a healthy market all round.
You will have noticed that it doesn't take much to tip a seesaw. There are unpredictable factors like plant diseases, catastrophic climatic events, and political unrest, though their unpredictability does not include the likelihood that one or other will not happen in the forseeable future. If I had to identify a single facor that might make the nightmare scenario of my earlier question come true, it would be the emergence of another large but presently dormant market. If the USA embargo against Cuba continues, Altadis will naturally look to somewhere like China for expansion. A market growth for Cuban cigars might reasonably be expected to drive a growth in the sales of non Cuban cigars. Higher demand without increased availability (remember the tobacco farmer to the cigar roller lead times) brings about scarcity and higher prices.
The next famous hoarding in Picadilly may one day be, "What Price Churchills?"
http://tinyurl.com/vgs76