To be “on the skids” means to be down on your luck and still falling.
In the early twentieth century, skids were greased wooden runways used on dirt roads by the forest industry to make it easier to move logs from the bush to the river or the sawmill.
The depressed street these skid roads passed through in a lumber town were lined by bars and flophouses where the transients looking for work lived, and so it was called “skid row.”
