I think you are underestimating the Old Crow, putting today's product in the past. Old Crow was once the most famous brand in America and known for quality. It was not until the 1970's that the quality really fell to the present level. In the 1940's it was at least on the level with Old Taylor and Old Grand Dad.
If you think the prices are low in the 1940's you should see them in the 1870's. E H Taylor, Jr. is selling OFC at three years old at $1.10 per gallon. Of course you had to buy the whole barrel since he did not bottle his own product, but I would not paying $50.00 for a barrel of fine bourbon that I could then let age as long as I wished. He even made sure the barrel was a presentation piece with brass hoops and an attractive brand on the head.