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2006 Deep Time from Hundred Acre. Drinking well.

What's your favorite red wine?
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If you want to gamble for fun, set aside an amount and don't feel bad if it tanks. Using platforms for alt investments like masterworks or Vinovest are higher risk than the marketing will let on, and should not be a significant part of your investment portfolio.
Curious about what you expect you’ll learn about wine from gambling on the price appreciation of bottles you’ll never touch nor drink? It’s almost no different than a barrel of oil at that point.
Most efficient way to learn about wine is to taste a lot of it. Wine shops that operate a paid tasting system are the best place to start, e.g the Sampler for those in the UK (https://thesampler.co.uk/pages/sampling), which I’m sure must also exist in the US and Europe etc.
Fair enough, though it’s more fun to hold those wines as an investment in your own future enjoyment (at a lower cost point than buying an earlier vintage to drink immediately) than to try and profit from them.
As a general proposition 5 years is not long at all in the wine world if you’re talking about what 2022 vintages are worth holding on to in till 2027+. I think even most reviews/scores involve a degree of crystal ball gazing, and are essentially scoring future potential rather than how good they are for drinking immediately on release (eg a 97point top end 2021 Barolo is unlikely to be particularly pleasant right now).
I’d say that most half-decent red wine, including most Napa Cabs and Oregon Pinot, will improve at-least marginally over that time span (and peak between 10 and 30years), and become more expensive assuming that vintage sold out at release. As such id focus on buying the best wines that you can afford now, but would probably not be willing to pay twice the price for in 5 years.