As a thought experiment, I've just sold a bottle of G-D Cote Brune '91 for £1400 for which I paid £40 or so a few years ago. Obviously I bought it with the intention of trying an interesting wine made in a way that's very rare now and in a style I have generally liked and enjoyed.
With the thought proceeds I've just bought two cases of Charles Heidsieck Mis en Cave, a case of Aleth le Royer-Girardin Pommard Rugiens 2001 and a six pack of Rostaing Cote Blonde 2013 all of which wouldn't normally get a look in as my funds are limited (I'm not crying poor mouth, simply stating that everyone has a limit to their funds) and I have allocated those resources elsewhere.
By way of regret, I will now never get to experience that particular peice of history and I suppose that in order to better understand the wines of the Northern Rhone fully (an area of great interest to me) I really ought to taste this particular wine. A great part of this wine's utility to me lies in its ability to provide a broader context to my future drinking of any of the wines of the region.
On the plus side I get three cases of really excellent wine that are ready to drink now, all of which could fuel many really fun times with friends and family and a six pack of a future potentially top-of-the-line Northern Rhone in my cellar. Additionally I get the relief of removing an insurance liability. My insurance covers individual bottles up to the value of £500. Beyond that I'm on my own, or I have to potentially purchase further insurance.
The dilemma probably wouldn't exist if I had several bottles, as I could sell all but one (my real problem isn't in the morality of selling wine when it's ridiculously valuable), more that in only owning a single bottle the and selling the potential experience is gone for good.
What to do?