It has been about 16 months since I've made a "what's my bottle worth" post. It's a question I get all the time.
“How much?” is a tricky subject with old liquor bottles because it is illegal to sell alcohol without a license. There are collectors, they buy and sell, and I haven’t heard of anyone being prosecuted for it, but because it is illegal most transaction are on the down low.
A precondition for assessing the resale value of anything is a sufficiently active secondary market for the type of object being assessed. An assessor studies recent sales to predict future prices. The secondary market for American whiskey is too small, fragmented and secretive to do that.
The only easily-accessible market for this sort of thing is the auction web site eBay.
The rarest and most valuable bottles are the oldest ones. Some post-Prohibition bottles have value, usually because the distillery where they were made is out-of-business. Prohibition-era medicinal whiskey is surprisingly common. Rarest of all are intact (i.e., full and well-sealed) pre-Prohibition bottlings.
The absolute high end on eBay is maybe $1,000, and that is only if you get lucky and a couple of people really want what you're selling.
There is a subset of this market that specializes in limited editions by particular producers, Jack Daniel's and Maker's Mark primarily. While most items sell in the sub-$500 range, there is no saying what the top end is. Naturally, big money transactions are the most secretive of all.
Among the people who buy old whiskey, many do it to drink the stuff. This tends not to be true of the Daniel's and Maker's Mark collectors.
I hope this is helpful.