When the label doesn't reflect the contents

The most expensive bottle I've ever opened was a 1952 Burgundy from a very high-end producer and worth a hefty six-figure sum. It was sublime, with all the depth and nuance you'd expect from a mature 60 year old.
But was it really 60 years old? Was it really a grand cru Burgundy from this specific producer? I couldn't tell you. Counterfeit wines (especially in this specific price group) is on the rise. It could have been a really good re-bottled négociant (Up until the -70s large producers in Burgundy would sell their output in bulk to so called négociants which would bottle and sell it under their own labels). I didn't check for the initials "RK" on the bottom of the bottle, but I sure as hell am going to pick that practice up.
See, the only people who can really know if an old, expensive bottle is the real deal are the producers themselves, and that's not by taste. Badly made fakes are of course easy for most of us to figure out, but the well made ones pull the wool over the eyes on even the most acclaimed experts. They can make an educated guess, of course, which is better than most people's gargling and spitting. However, one mostly has to rely on the producers themselves and their records of making, bottling and selling the wine. I remind you that this was before the internet generation and the FBI's division specializing on frauds concerning art. So the records are sketchy. After all, how difficult can it be to take an old, empty bottle and fit it with a fake label? Not too difficult, considering that some producers could't even spell their own names properly.

I guess it boils down to "is wine ever really worth these very large sums of money?". Let me put it this way: no.
To me, if I had a couple of millions to drop in the murky world of wine auctions then yes, I'd drop them right in there on a bottle once owned by the Shah of Iran. But if you drink wine like I do, you're much better off investing in selected bottles for those special occasions, and a couple of steady house wines. It saves you stress, or at least it saves me a lot of stress. To my mind, wine is one of those things that should never be spoiled by stress and anxiety. How do you judge whether the time is right to open your 1950's grand cru Burgundy? It's not like there's an unlimited supply should your date be bad.