Well, to be blunt, none of the signors are deceased so I'd hang on to them a bit longer. Best price I've seen for the Manual (unsigned) is $10. So, if you really needed to sell I recommend an Ebay "Buy it Now" for $40 with a "Best Offer" option included. Costs nothing for listing but will cost a % to Ebay if you accepted an offer.
As to the 1995 Star Trek Calendar, the best time to sell this would be 2016 as the following year (2017) is an exact match to the 1995 calendar days and would, at that time, be 21 years old, which is pretty much a bare minimum for a collectible these days, considering how may are produced.
Thanks for the education. Wondered about the deceased vs. living status myself, but decided the whole thing was worth at least throwing that line into the surf to see what was out there. Appreciate the comeback.