I don't know how relevant this is but I planted some Asiatics, Tulips and Crocus in an old whiskey barrel once and everything died. I had it placed on an elevated deck about 12 inches above ground level. All the drain holes I made froze shut over winter and they were the last thing to thaw out in the spring. When heavy spring rains came, the whole thing overflowed with water that froze and thawed many times; then one morning I got up to see all the water had gone overnight. It remained a barrel of mud for days.
If I were to do it again, I would make sure my soil is fairly dry, then I'd cover with a tarp to make it rain proof and throw lots of snow from the deck around and on top of the covered barrel.
