Get with some local clubs and I’m A Simple Woman Beer And Hockey shirt that will get you a sample of some of those really coveted bottles. Or find a decent deal at a bar and splurge a bit. I assure you that after you’ve had a taste of EHT 18 Year Marriage or PVW 23 or W12 or whatever other super coveted bottle that comes around, you’ll quickly get over your FOMO. They just aren’t that good and if you’re in it for the buying/selling aspect of it, you can make more money with less risk by putting your money/energy elsewhere.
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I have my couple no-longer-produced bottles that I’m A Simple Woman Beer And Hockey shirt for (mostly my favorite Booker’s batches), but as for new stuff? I don’t try and don’t care any longer. I can get Old Forester 1920 and Evan Williams BiB anytime I want for a great price. After that, there is a whole world of available bourbon that I haven’t gotten to try yet that I don’t have to bend over backwards for.