Oh it matters ...
I have, somewhere, a PRR T&HS article about Long Island cabs .... very interesting saying, among other things, that they were never turned, except by mistake. In winter, the crew wanted that heater and whatever insulation they had stuffed into it on the windward side.
In the days when a caboose was almost personal property of a senior crew member, I wouldn't be surprised if the same was not true on many other roads.