While others may not believe that Jack is worth while collecting, it is still a option for many people. If you want to start collecting, give thought and consideration to the Medals Series or if you want to go all out try and get a decanter which is sealed, in box with unregistered tags.
If you are serious about collecting invest in a Jack Daniels Collectors Book which is available on Ebay from a Seller called Cowboy Jack. This will give you a full list of the bottles that are available to collect.
Only other comment I would make is that Whiskey will age better and could result in stronger returns based upon your purhcases. Be careful in your purchases, its similiar to that of the Stock Exchange, a return is not guaranteed.