One year ago I mixed a batched Manhattan Island and aged it in a TEN30 barrel I've used to age multiple Manhattan variations. My version was made with Hennessy VSOP, Cocchi di Torino vermouth and Luxardo cherry liqueur.
I made this with Wild Turkey 101 that I finished in a 1 liter oak cask conditioned with Cabernet Sauvignon. No fresh wine. That said, this was a delicious cocktail that was different enough from a Brooklyn to make it a little interesting. Not sure its worth aging bourbon just for this cocktail, but I'd definitely experiment if I had a nice bottle of red I'm either finishing (or starting).
The overproof rum really does make this. Just did a 500ml batch freezer door version using Doorly's 12, Wry and Nephew white over proof, Bitter Truth falernum and coconut water for dilution (pour straight from the bottle over ice, so dilution is needed for a batched cocktail). Really nice. I'm going to experiment with adding Stiggin's Fancy, too.
Exquisite!