Expectation...

After a few...recent experiences with both wines and cigars I got to thinking about how, and under what circumstances, you actually best enjoy bottles or cigars and how to avoid disappointments. I think it is fair to say that high levels of expectation are probably the biggest villain when it comes to feeling let down. This isn't to say that I believe being a pessimist is the way to go. At the price of wine today "expect nothing and you might be surprised" is hardly going to work or give satisfaction. I do think that there are some things you can do to maximise pure enjoyment of wines (and cigars for that matter). Some of the best moments have been with almost no expectation and often with little or no planning. A bottle of Montrose 1975 I was given (my birth year) is a particularly good memory. Now this is no great wine, good yes and fun but nothing serious, I loved the bottle because I got back from a crappy day and drank it with some bread and houmous probably far more quickly than I should have but it gave great pleasure and was a spontaneous act.
Anyhow here a list of a few things that I think can help maximise enjoyment:

Always have access to some good bottles...so that when the moment grabs you you can drink one or two, having great/interesting/exciting wine when you really crave it is a wonderful thing. Don't worry about maturity too much. This can be dangerous as we've all opened great bottles late at night when they can't be appreciated but I think it is crucial to facilitate impulses by having wine about.

Don't buy just the "best" wines, this sounds odd but the "best" has high expectation built in already. I'd say 5-10% of any collection or stash should be classed as "not quite sure why I bought that but..."

Don't buy just the best vintages...I think this could be the most important point...find producers/regions you love and buy them each year. Never be afraid of the "4star" vintage. If you took Bordeaux as an example then you could make an argument for having bought just 2000, 2005, 2009 & 2010 and that could last you 40+ years but you'll expect a lot from them all and you're missing gems from almost all the other vintages especially 2001, 2006 & 2008. I haven't even mentioned the money you could save. Consider buying bigger bottles in "perceived to be lesser" years.

Beware the top "cuvee"...this might be straying from the point but expecting much more from the Riserva than the normale or the Vielles Vignes from the standard bottling can be cause for disappointment, clearly it depends on the area, terroir and producer but be wary of the premium.

Forget what you paid...ok ok very easy (and it is a little tongue in cheek) to say but a bit like betting, write the money off when you buy the wine, it'll make you more generous with when to serve things, less precious and value can be over stressed at times. Referring back to price is baggage you don't need.

Take a back up...if going to dinners or Paulee type scenarios, it takes the stress out of things and also makes you braver about taking a wine you may be nervous about but then really enjoy.

Keep the food simple when opening exciting bottles...applies especially if you are cooking/hosting. I feel strongly that much as food and wine are great bedfellows you can't focus on both at once. Great ingredients cooked simply works - no surprise there then!

Buy in cases not singles the "six pack" has meant you can buy more different wines easily but I am very wary of buying less than 6 bottles of something to give a bit of time too. You can't get to know one bottle but can enjoy and get to know a case. Often opening something that you have had before lessens expectation (and therefore increases enjoyment).

Good glasses but less pomp and ceremony...not much needs adding, I think a little like the simple food idea, good glasses and the correct serving temperature (warmth has killed more reds than corkiness I'd say) is crucial but anymore is a pain.

It's not a competition...drink with people you like and take bottles you are comfortable with opening. If you feel under pressure to spend more than you are happy with then I would say you're drinking with the wrong people. And much as there is often a stand out wine at a dinner etc I try hard to avoid the "wine of the night" type decisions...wine is varied and personal and should, to my mind, remain so...