I would have gone with a new unique/benchmark experience. From my experiance the ‘76 &’ 01Yquem, 82 PLL and the 1968 Mastrobearadino Taurasi Riserva would have all been the meet that goal. I would love to have those again…but only the '01 Yquem remains…
Given that I have a lot of good wine, I probably would go for one bottle (maybe add some money) and get an Haut Brion.
If we are going to play this game, I would go back in time to 2002, revisit the Truchots and get their grand crus at the winery for 22 euros. Or go back to the early 1980s, go to Bassins and get 1980 DRC Grands Echezeaux for $35.
a Rinaldi with a big of age would be my single bottle choice as well
in the 2-3 range, would probably be a La Mission from a decent vintage, or a Dujac 1er Cru that fits the bill
if im going multi bottles, I’d send all of it to Joel Peterson and tell him to send me however much old Ravenswood that buys.
Drouhin without a doubt
2 bottles of Springbank 15, some Foursquare Rum, and a bottle of Kilkerran 12.