From looking at that picture, you would not have recognized the Lookout House before it burned down. It had grew into a fancy place.
A little history: Gambling roughly 1933 to 1951. Gambling was ran by Jimmy Brink who also owned The Lookout Stud Farm, until Moe Dalitz and the Cleveland Syndicate took it away from him.

The Lookout House sat at the top of a 3 or 4 mile hill on Dixie Highway RT US25 that ran to Florida.
Not sure what it was during the civil war but it was one of the central points in the underground railroad. It had tunnels running parallel to US 25 that ran down the hill to the Ohio River. There were several rooms at the beginning to the tunnel. There was an after hours joint in the rooms for awhile after the fire. It was all candlelit. Dank, dark, and the walls seeped water.
It was scary down there. I always felt like Dracula was going to jump out from around a corner.
Lookout House gambling closed in 1951, thanks to the Kefauver Commission. By the time I went to the Lookout House in roughly 1962, it was a classy night club catering to the elite of N KY and Cincinnati. Burned in 1973.