Wow where did you get the whiskey barrel? I would think that eventually the wood would swell up and fix those leaks.
I finally found one on Craigslist. Actually, I found plenty of them, but they were all either signed by the distiller and made into expensive furniture or sold before I got to them. The one I bought I happened to see about 20min after she posted it.
I figured it might seal up, but maybe not. One of the leaks was bad enough that no water would stay behind it, the water would had to have wicked up the wood (which it probably would have eventually). I kind of like the bag as a liner for cleanup idea anyway.