Having been twice in Cuba 12 and 8 years ago on official UN and European Union consulting business (I wasn't a US citizen then) and being a full fledged cigar smoker since 1990, I believe I can give you some reliable info, notwithstanding the fact that things may have changed:

After mentioning casually to the seminar organizer, a pleasant Margaret Thatcher looking high ranking civil servant with rather bad teeth, she suddenly found she had no more urgent business than supplying me with what I had on my list: I named about 5 brands and modules, indicated that I wished to buy about about 100 units total, and she disappeared from the seminar (where she should have been present) to come back about 2 hours later with the exact content of the list, for which she charged me about $ 70. No doubt that she got them through her privileged status and made some money on the transaction since this is how Cuba works. Nomenklatura is not ONLY a Russian word.

I checked the public price (every Cuba hotel, upscale or not has a cigar shop), and it came to close to $ 400.

Every kid walking on the Malecon, Havana's seaside promenade, offers you brand cigars which look like the real thing (after offering their sister, mother, BROTHER, rum etc...) at very competitive prices, but I would not trust them, considering that 90% of Cuban brand cigars offered in Santo Domingo including in nice looking shops are unsmokable abominable fakes. I had no problem taking them out and flying back with them as I was going to France which has no embargo against Cuba.

If things have not changed, public prices in reliable shops in Cuba are about 40% of the prices in Western Europe.

This being said, do not forget that Cuban cigars are ILLEGAL in the US, that those offered there at outrageous prices are most likely fakes, and that reputable shops in France and Switzerland give you OPEN boxes with a paper stating that the boxes have been opened for quality control. My sources tell me that those stores (Davidoff, La Civette, Harrods etc... ) have a reject rate of close to 50 %. if you were a quality control cigar supervisor in Cuba and were paid about $ 20 per month, would you work very hard ? That is the whole question. As to me, I have switched to Dominicans.

Good Luck