I think it comes down to people's situation and the cigars themselves. Cuban cigars will never be sold at a lost unless the buyer was an idiot and severely overpaid.
Look at certain RE boxes that are considered "really good" by enthusiasts such as Conde 109, PL Mags, LGC Gloriosos, RA Gladiator, etc....those boxes rarely surface and when they do they command exorbitant pricing, I don't see these ever flooding the market in the future.
While on the flip side there are tons of RE and LE that are still available because people don't care for them, volumes produced and pricing.
For the most part, Cohiba LE's is an exception to this rule as these will sell for 3-5x original price in a short time period, look at 1966 and Supreme Robustos pricing now...and how the Talisman will continue this streak.
How about regular production? I think a good cigar is a good cigar no matter the brand or year. Some regular production smokes will increase in value year over year more than others, some examples are:
98 Punch Monarcas, 2013 Cohiba, 2011 Serie E, 05 ERDM, lots of 2013 stock, etc. ....all of these examples command extremely high prices and rarely seen publicly for sale
Lots of regular production cardboard packs available today from 99-01, available because they are crap IMHO
So in summary I think it comes down to the cigars themselves rather if they are RE, LE or regular production when it comes down to investments.
Just my two cents from someone that regularly smokes, ages his own cigars and occasionally sells cigars.